Phenylpyrazole herbicides

ABSTRACT

Compounds of formula I ##STR1## wherein the substituents R 1  and R 6  and n are as defined in claim 1, and the salts and stereoisomers of the compounds of formula I have good pre- and post-emergence selective herbicidal properties. 
     The preparation of those compounds and their use as herbicidal active ingredients are described.

The present invention relates to novel, herbicidally active phenylpyrazole derivatives, to processes for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants or in the inhibition of plant growth.

Pyrazole compounds having herbicidal action are known and are disclosed, for example, in EP-A-0 361 114, JP-A-03 093 774, JP-A-02 300 173 and JP-A-03 163 063.

Novel phenylpyrazole derivatives having herbicidal and growth-inhibiting properties have now been found.

The present invention therefor relates to compounds of formula I ##STR2## wherein

R₁ is C₁ -C₄ alkyl;

R₂ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl or C₃ - or C₄ -alkynyl;

n is 0, 1 or 2;

R₃ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl, C₃ - or C₄ -alkynyl, --CH₂ --COOH, --CH₂ COO--C₁ -C₄ alkyl or --CH₂ CN;

R₄ is hydrogen, fluorine, chlorine or bromine;

R₅ is hydrogen, methyl, trifluoromethyl, cyano, nitro, amino or C₁ -C₄ haloalkoxy;

R₆ is hydrogen, halogen, cyano, NHR₁₀, NR₁₀ R₁₁ or SO₂ Cl;

R₁₀ and R₁₁ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₃ -C₆ cycloalkyl, C₁ -C₈ haloalkyl, C₃ -C₈ haloalkenyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₆ is OR₂₀ ;

R₂₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, ##STR3## C₃ -C₈ haloalkenyl, C₃ -C₆ cycloalkyl, ##STR4## C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylamino-C₁ -C₄ alkyl, di-C₁ -C₄ alkylamino-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, those aromatic and heteroaromatic rings being unsubstituted or mono- or tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₂₀ is C₁ -C₈ alkyl-COXR₂₁ or CH(C₆ H₅)COXR₂₁ ;

X is oxygen, sulfur or NR₂₂ ;

R₂₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl, mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C₁ -C₄ alkyl or by halogen; and

R₂₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ alkenyl; or

R₆ is S(O)_(m) R₃₀ ;

m is 0, 1 or 2;

R₃₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₈ haloalkenyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- or tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₄ alkyl-COVR₃₁ ;

V is oxygen, sulfur or NR₃₂ ;

R₃₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; and

R₃₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ ; or

R₆ is COR₄₀ ;

R₄₀ is hydrogen, chlorine, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₈ haloalkenyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₆ is COYR₅₀ ;

Y is oxygen, sulfur, NR₅₁ or NOR₅₄ ;

R₅₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, ##STR5## C₃ -C₈ haloalkenyl, C₃ -C₆ cycloalkyl, ##STR6## C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, C₁ -C₄ alkyl-COZR₅₂, C₃ -C₆ cycloalkyl-COZR₅₂, C₁ -C₄ alkyl-CO--C₁ -C₄ alkyl or C₁ -C₄ cyanoalkyl;

Z is oxygen, sulfur, NR₅₃ or NOR₅₅ ;

R₅₂ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, ##STR7## C₃ -C₈ haloalkenyl, C₃ -C₆ cycloalkyl, ##STR8## C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₁ and R₅₃ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₄ and R₅₅ are each independently of the other C₁ -C₄ alkyl; or

R₆ is ##STR9##

R₅₆ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl or C₃ -C₈ alkynyl;

R₅₇ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl or C₃ -C₈ alkynyl or C₁ -C₄ alkylcarbonyl; or

R₆ is C₁ -C₈ -B, C₁ -C₈ haloalkyl-B, C₂ -C₈ alkenyl-B, C₂ -C₈ alkynyl-B, C₂ -C₈ haloalkenyl-B, C₁ -C₄ alkoxy-C₁ -C₄ alkyl-B or C₁ -C₄ alkylthio-C₁ -C₄ alkyl-B; and

B is hydrogen, --COZR₅₂, cyano or C₁ -C₄ alkyl-C(O)--, and the salts and stereoisomers of the compound of formula I.

The present invention relates also to compounds of formula I wherein

R₁ is C₁ -C₄ alkyl;

R₂ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl or C₃ - or C₄ -alkynyl;

n is 0, 1 or 2;

R₃ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl, C₃ - or C₄ -alkynyl, --CH₂ --COOH, --CH₂ COO--C₁ -C₄ alkyl or --CH₂ CN;

R₄ is hydrogen, fluorine, chlorine or bromine;

R₅ is hydrogen, methyl, trifluoromethyl, cyano, nitro, amino or C₁ -C₄ haloalkoxy;

R₆ is hydrogen, halogen, C₁ -C₅ alkyl, C₁ -C₅ haloalkyl, C₂ -C₅ alkenyl, C₂ -C₅ haloalkenyl, C₂ -C₅ alkynyl, C₂ -C₅ haloalkynyl, cyano, NHR₁₀ or NR₁₀ R₁₁ ;

R₁₀ and R₁₁ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₃ -C₆ cycloalkyl, C₁ -C₈ haloalkyl, C₃ -C₈ haloalkenyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₆ is OR₂₀ ;

R₂₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, those aromatic and heteroaromatic rings being unsubstituted or mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₈ alkyl-COXR₂₁ ;

X is oxygen, sulfur or NR₂₂ ;

R₂₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl, mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C₁ -C₄ alkyl or by halogen; and

R₂₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ alkenyl; or

R₆ is S(O)_(m) R₃₀ ;

m is 0, 1 or 2;

R₃₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₄ alkyl-COVR₃₁ ;

V is oxygen, sulfur or NR₃₂ ;

R₃₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; and

R₃₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ ; or

R₆ is COR₄₀ ;

R₄₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₆ is COYR₅₀ ;

Y is oxygen, sulfur, NR₅₁ or NOR₅₄ ;

R₅₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₄ alkyl-COZR₅₂ ;

Z is oxygen, sulfur, NR₅₃ or NOR₅₅ ;

R₅₂ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₁ and R₅₃ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₄ and R₅₅ are each independently of the other C₁ -C₄ alkyl; or

R₆ is C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₂ -C₄ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂,

and the salts and stereoisomers of the compound of formula I.

The present invention relates also to compounds of formula I wherein

R₁ is C₁ -C₄ alkyl;

R₂ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -haloalkenyl or C₃ - or C₄ -alkynyl;

n is 0, 1 or 2;

R₃ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl or C₃ - or C₄ -alkynyl;

R₄ is hydrogen, fluorine, chlorine or bromine;

R₅ is hydrogen, methyl, trifluoromethyl, cyano, nitro, amino or C₁ -C₄ haloalkoxy;

R₆ is hydrogen, halogen, cyano, NHR₁₀, NR₁₀ R₁₁ ;

R₂₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, those aromatic and heteroaromatic rings being unsubstituted or mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₈ alkyl-COXR₂₁ ;

X is oxygen, sulfur or NR₂₂ ;

R₂₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkynyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl, mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- or tri-substituted by C₁ -C₄ alkyl or by halogen; and

R₂₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ alkenyl; or

R₆ is S(O)_(m) R₃₀ ;

m is 0, 1 or 2;

R₃₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₄ alkyl-COVR₃₁ ;

V is oxygen, sulfur or NR₃₂ ;

R₃₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; and

R₃₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ ; or

R₆ is COR₄₀ ;

R₄₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₃ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; or

R₆ is COYR₅₀ ;

Y is oxygen, sulfur, NR₅₁ or NOR₅₄ ;

R₅₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, or C₁ -C₄ alkyl-COZR₅₂ ;

Z is oxygen, sulfur, NR₅₃ or NOR₅₅ ;

R₅₂ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₁ and R₅₃ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen;

R₅₄ and R₅₅ are each independently of the other C₁ -C₄ alkyl; or

R₆ is C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₂ -C₄ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂,

and the salts and stereoisomers of the compound of formula I.

In the above definitions, unless otherwise indicated halogen is to be understood as being fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.

The alkyl, alkenyl and alkynyl groups may be straight-chained or branched, and this applies also to the alkyl, alkenyl and alkynyl moiety of alkylcarbonyl, haloalkyl, haloalkoxy, haloalkylcarbonyl, haloalkylphenyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylthio, alkenylthio, alkynylthio, alkylsulfonyl, alkylsulfonyl, haloalkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkylphenyl, alkylamino, dialkylamino, alkylaminocarbonyl-alkyl, alkylthio-alkoxycarbonyl, alkylthiocarbonyl-alkyl, alkenylthiocarbonyl, alkynylthiocarbonyl, haloalkoxycarbonyl-alkyl, alkylcarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl and alkoxycarbonyl-alkyl groups.

Examples of alkyl groups that may be mentioned are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and the various isomeric pentyl, hexyl, heptyl and octyl radicals, preferably alkyl groups having from 1 to 4 carbon atoms.

Examples of alkenyls that may be mentioned are vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl, 2-hexenyl, 3-heptenyl and 4-octenyl, preferably alkenyl radicals having a chain length of from 3 to 5 carbon atoms.

Example of alkynyls that may be mentioned are ethynyl, propargyl, 1-methylpropargyl, 3-butynyl, but-2-yn-1-yl, 2-methylbutyn-2-yl, but-3-yn-2-yl, 1-pentynyl, pent-4-yn-1-yl and 2-hexynyl, preferably alkynyl radicals having a chain length of from 2 to 4 carbon atoms.

Suitable as haloalkyl are alkyl groups mono- or poly-substituted, especially mono- to tri-substituted, by halogen, with halogen being in particular iodine and especially fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,22-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl.

Suitable as haloalkenyl are alkenyl groups mono- or polysubstituted by halogen, with halogen being in particular bromine, iodine and especially fluorine and chlorine, for example 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluoro-but-2-en-1-yl and 4,4,4-trichloro-but-2-en-1-yl. Of the C₂ -C₅ alkenyl radicals mono-, di- or tri-substituted by halogen, preference is given to those having a chain length of 3 or 4 carbon atoms. The alkenyl groups may be substituted with halogen at saturated or unsaturated carbon atoms.

Haloalkenyl in the definition of R₆ as haloalkenylCOZR₅₂ is, for example, 1,2-dichloroethenyl or 1,2-dibromoethenyl.

Suitable as haloakynyl are, for example, alkynyl groups mono- or poly-substituted by halogen, with halogen being bromine, iodine and especially fluorine and chlorine, for example 3-fluoropropynyl, 3-chrloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluoro-but-2-yn-1-yl.

Carboxyalkyl is, for example, carboxymethyl, carboxyethyl, carboxyeth-1-yl and carboxypropyl.

Alkoxyalkyl is, for example, methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl, ethoxyethyl, propryethyl, butoxyethyl, methoxypropyl, ethoxypropyl or propoxypropyl.

Alkoxy is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy.

Alkenyloxy is, for example, allyloxy, methallyloxy and but-2-en-1-yloxy.

Alkynyloxy is, for example, propargyloxy and 1-methylpropargyloxy.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.

Alkenyloxycarbonyl is, for example, allyloxycarbony, methallyloxycarbonyl, but-2-en-1-yl-oxycarbonyl, pentenyloxycarbonyl, 2-hexenyloxycarbonyl and 3-heptenyloxycarbonyl.

Alkynyloxycarbonyl is, for example, propargyloxycarbonyl, 3-butynyloxycarbonyl, but-2-yn-1-yl-oxycarbonyl and 2-methylbutyn-2-yl-oxycarbonyl.

Alkylamino is, for example, methylamino, ethylamino and the isomeric propylamino and butylamino.

Dialkylamino is, for example, dimethylamino and the isomeric dipropylamino and dibutylamino.

Alkenylamino is, for example, allylamino, methallylamino and but-2-en-1-yl-amino.

Alkynylamino is, for example, propargylamino and 1-methylpropargylamino.

Cycloalkyl radicals that come into consideration as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkoxyalkoxycarbonyl is, for example, methoxymethoxycarbonyl, ethoxymethoxycarbonyl, ethoxyethoxycarbonyl, propoxymethoxycarbonyl, propoxyethoxycarbonyl, propoxypropoxycarbonyl, butoxyethoxycarbonyl and butoxybutoxycarbonyl.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy.

Haloalkylamino is, for example, chloroethylamino, trifluoroethylamino and 3-chloropropylamino.

Di(haloalkyl)amino is, for example, di(chloroethyl)amino.

Alkylthioalkyl is, for example, methylthioethyl, ethylthioethyl, methylthiopropyl and ethylthiopropyl.

Alkenylthiocarbonyl is, for example allylthiocarbonyl, methallylthiocarbonyl, but-2-en-1-yl-thiocarbonyl.

Phenyl, benzyl or benzoyl as part of a substituent such as phenoxy, phenoxycarbonyl, phenoxycarbonylalkyl, benzoylamino or benzylamino is unsubstituted or substituted. The substituents may then be in the ortho- meta- or para-position. Substituents are, for example, C₁ -C₄ alkyl, halogen, C₁ -C₄ haloalkyl, cyano, nitro, hydroxy, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, amino, C₁ -C₄ alkylamino, di-C₁ -C₄ alkylamino, carboxyl, C₁ -C₄ alkoxycarbonyl, carbamoyl, C₁ -C₄ alkylaminocarbonyl or di-C₁ -C₄ alkylaminocarbonyl.

Corresponding meanings can be assigned also to the substituents in combined definitions, for example cycloalkyl-oxy, cycloalkyl-thio, cycloalkylcarbonyl, cycloalkyl-oxycarbonylalkyl, phenylalkyl, phenylalkenyl, alkoxycarbonylaklyl, alkenyloxycarbonylalkyl, alkynyloxycarbonyl-alkyl, haloalkoxycarbonyl-alkyl, alkylaminocarbonyl-alkyl, alkenylaminocarbonyl-alkyl, alkynylaminocarbonyl-alkyl, dialkylaminocarbonyl-alkyl, alkoxyalkylamino, alkoxyalkylaminocarbonyl-alkyl, dialkoxyalkylamino, alkoxyalkoxycarbonyl, alkoxyalkoxycarbonyl-alkyl, alkylaminocarbonyl, alkylthiocarbonyl, alkylthio-alkyl, , alkylthiocarbonyl-alkyl and haloalkoxycarbonyl-alkyl, and also for the combined definitions of the hydroxamic acid derivatives, such as, for example, for R₆ ═CON(R₅₀)OR₅₄ or R₆ ═COY-C₁ -C₄ alkyl-CON(R₅₂)OR₅₅.

Salts of the compounds of formula I with acidic hydrogen, especially the derivatives with carboxylic acid groups (for example carboxy-substituted alkyl and phenyl groups) are, for example, alkali metal salts, for example sodium and potassium salts; alkaline earth metal salts, for example calcium and magnesium salts; ammonium salts, that is to say unsubstituted ammonium salts and mono- or poly-substituted ammonium salts, for example triethylammonium and methylammonium salts; or salts with other organic bases.

Of the alkali metal and alkaline earth metal hydroxides as salt-forming agents, special mention should be made, for example, of the hydroxides of lithium, sodium, potassium, magnesium or calcium, but especially those of sodium or potassium.

Examples of amines suitable for ammonium salt formation are both ammonia and primary, secondary and tertiary C₁ -C₁₈ alkylamines, C₁ -C₄ hydroxyalkylamines and C₂ -C₄ alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, thiomorpholine, N-methylmorpholine, N-methyl-thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethosyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.

Salts of the compounds of formula I with basic groups, especially the derivatives with amino groups, for example alkylamino, dialkylamino or alkenylamino, are, for example, salts with inorganic and organic acids, for example hydrochloric acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, and also sulfuric acid, phosphoric acid, nitric acid and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, axalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid and salicylic acid.

The possible present of at least one asymmetric carbon or sulfur atom in the compounds of formula I, for example in the substituent R₆ ═OR₂₀ wherein R₂₀ is a branched alkyl, alkenyl, haloalkyl or alkoxyalkyl group, or R₆ ═S(O)_(m) R₃₀ wherein, for example, m=1 and/or R₃₀ is a branched alkyl, alkenyl, haloalkyl or alkoxyalkyl group, means that the compounds can occur both as optically active individual isomers and in the form of racemic mixtures. In the present invention, the compounds of formula I are to be understood as including both the pure optical antipodes and the racemates or diasteroisomers.

If an aliphatic C═C double bond is present, geometric isomerism may occur. The present invention relates also to those isomers.

Preference is given to compounds of formula I wherein R₅ is chlorine, bromine, methyl, trifluoromethyl or cyano.

Preference is given also to compounds of formula I wherein R₆ is hydrogen, halogen, OR₂₀, S(O)_(m) R₃₀ or COYR₅₀.

Compounds of formula I wherein n is 0 or 2 are also preferred.

Compounds of formula I wherein R₁ is methyl are also preferred.

Preference is also given to compounds of formula I wherein R₂ is methyl.

Also preferred are compounds of formula I wherein R₃ is methyl or ethyl.

Compounds of formula I wherein R₃ is methyl are especially preferred.

In a group of very especially preferred compounds of formula I, R₄ is fluorine.

In a further very especially preferred group of compounds of formula I, R₄ is hydrogen.

In another very especially preferred group of compounds of formula I, R₄ is chlorine.

In a further group of very especially preferred compounds of formula I, R₄ is chlorine; and R₆ is OR₂₀ wherein R₂₀ is as defined for formula I.

A group of very especially preferred compounds of formula I comprises compounds wherein R₄ is fluorine; and R₆ is OR₂₀ wherein R₂₀ is as defined for formula I.

Further groups of very especially preferred compounds of formula I comprise compounds wherein R₄ is chlorine; and R₆ is S(O)_(m) R₃₀ wherein R₃₀ and m are as defined for formula I.

In other groups of very especially preferred compounds of formula I, R₄ is fluorine; and R₆ is S(O)_(m) R₃₀ wherein R₃₀ and m are as defined for formula I.

A further group of very especially preferred compounds of formula I comprises compounds wherein R₄ is chlorine; and R₆ COR₄₀, COYR₅₀, C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₂ -C₄ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂ wherein R₄₀, R₅₀, R₅₂, Y and Z are as defined for formula I.

A further group of very especially preferred compounds of formula I comprises compounds wherein R₄ is fluorine; and R₆ COR₄₀, COYR₅₀, C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₂ -C₄ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂ wherein R₄₀, R₅₀, R₅₂, Y and Z are as defined for formula I.

In a further group of compounds of formula I that are likewise very especially preferred, R₅ is chlorine; and R₆ is --COYR₅₀.

Another group of likewise very especially preferred compounds of formula I comprises compounds wherein R₅ is chlorine; and R₆ is C₁ -C₄ alkyl-B or C₁ -C₄ haloalkyl-B.

The compounds of formula I ##STR10## wherein R₁ to R₆ and n are as defined for formula I can be prepared by means of processes known per se, for example by cyclising a compound of formula III ##STR11## wherein R₁, R₂ and R₄ to R₆ are as defined,

a) with hydrazine optionally in the presence of a suitable solvent to form a compound of formula IIa ##STR12## and then reacting that compound in the presence of a compound of formula Xa containing a corresponding C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₃ - or C₄ -alkenyl or C₃ - or C₄ -alkynyl group

    R.sub.3 --L.sub.1                                          (Xa),

the radical R₃ in the compounds of formula Xa being as defined for formula I and L₁ being a leaving group, preferably chlorine, bromine, iodine, CH₃ SO₂ O-- or ##STR13## optionally in the presence of a suitable solvent to form a compound of formula I ##STR14## wherein n is 0, and then oxidising that compound; or

b) with a compound of formula XI

    NH.sub.2 --NH--R.sub.3                                     (XI),

wherein R₃ is as defined, optionally in the presence of a suitable solvent, to form a compound of formula I ##STR15## wherein R₁ to R₆ are as defined, and n is 0, and the oxidising that compound.

The process according to the invention for the preparation of a compound of formula II ##STR16## wherein R₁, R₂, R₄ to R₆ and n are as defined for formula I, is carried out analogously to known processes and comprises halogenating a compound of formula IV ##STR17## optionally in the presence of a solvent and a base, for example acetic acid and sodium acetate, to form a compound of formula XII ##STR18##

R₁ and R₄ to R₆ in the compounds of formulae IV and XII being as defined and Hal being halogen, especially chlorine and bromine, and cyclising that compound of formula XII with a compound of formula XIII

    X.sub.2 N--NH--C(S)S--R.sub.2                              (XIII),

wherein R₂ is as defined, optionally in the presence of a solvent, for example an alcohol, for example ethanol, and a base, for example an alcoholate, for example an ethanolate, to form a compound of formula XIV ##STR19## which is not isolated, and then subjecting that compound to a ring contraction (extrusion reaction) (n=0) thermally or by acid catalysis, for example with 2N hydrochloric acid, and then oxidising the product (n=1 or 2).

The formation of the pyrazole rings of the compounds of formula I wherein n is 0, 1 or 2 is illustrated in more detail in Reaction Schemes 1,2 and 10 below. ##STR20##

The formation of the pyrazole rings of formula IIa that are unsubstituted at the nitrogen atoms (Reaction Scheme 1, Route a)) is carried about by reaction of the compounds of formula III with hydrazine or hydrazine hydrate optionally in the presence of a suitable solvent at elevated temperature, preferably with hydrazine hydrate in alcoholic solution at elevated temperature.

For the formation of the pyrazole rings that are substituted at the nitrogen atom (Reaction Scheme 1, Route b)), the procedure is analogous to that indicated under Reaction Scheme 1, Route a), with a compound of formula XI, for example N-alkylhydrazine, preferably N-methylhydrazine, being used as reagent.

The formation of the pyrazole rings of formulae II and IIa that are unsubstituted at the nitrogen atoms (Reaction Scheme 2) can be carried out, for example, also by halogenation of the compounds of formula IV preferably with chlorine or bromine optionally in the presence of a suitable solvent and a base, for example acetic acid and sodium acetate, subsequent cyclisation with a compound of formula XIII optionally in a solvent, for example an alcohol, preferably ethanol, and in the presence of a base, for example an alcoholate preferably an ethanolate, and ring contraction (extrusion reaction) analogously to known procedures, as described, for example, in Chem Ber. 92, 2593 (1959) or Acta Chem. Scand. 16, 2395 (1962). That method, described in Reaction Scheme 2, is suitable for the preparation of derivatives of formulae IIa and II that are substituted by halogen, especially by fluorine and chlorine, at the phenyl ring.

In certain cases it is advantageous to prepare the N-alkyl-substituted pyrazole derivatives, especially the N-methyl-substituted pyrazole derivatives, via N-alkylation of the corresponding unsubstituted pyrazoles of formula II (or IIa). Reaction Scheme 3 illustrates this. ##STR21##

In this Reaction Schemes 1, Route b), and 3, the radical R₃ in the hydrazine derivative of formula XI and in the alkylating agents of formulae Xa and Xb is as defined for formula I, and L₁ is a leaving group, for example chlorine, bromine, iodine CH₃ SO₂ O-- or ##STR22##

The N-alkylation of the pyrazole rings in the compounds of formulae II and IIa in Reaction Schemes 1 and 3 is carried out at room temperature or at slightly elevated temperatures in the presence of a solvent, for example acetone, methyl ethyl ketone, N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, a base, for example potassium carbonate, sodium carbonate, sodium hydroxide or potassium hydroxide, and an alkylating agent of formula Xa, Xb, preferably methyl iodide or dimethyl sulfate.

The selection of the suitable preparation method and the corresponding reaction conditions is made in accordance with the properties (reactivites of the substituents in the intermediates in question.

The subsequent oxidation of the compounds of formula I wherein n is 0 (Reaction Schemes 1 and 2) is carried out, for example, with peracids, for example m-chloroperbenzoic acid, or hydrogen peroxide in the presence of a suitable solvent, for example dichloromethane chloroform or carbon tetrachloride, at temperatures of from -40° C. to the reflux temperature of the solvent in question, preferably from 0° C. to 35° C. The degree of oxidation at the sulfur atom can be controlled by the amount of oxidising agent: in the case of an equimolar amount of oxidising agent, compounds of formula I wherein n is 1 are obtained and is the case of an excess (at least 2 mol) of oxidising agent, compounds of formula I wherein n is 2 are obtained.

The starting compound of formula III in Reaction Scheme 1 can be prepared analogously to known procedures, for example in accordance with the method given in Reaction Scheme 4 below: ##STR23##

The reaction in Reaction Scheme 4 is carried out, for example, analogously to WO 92/02509, according to which the phenylcarbonyl derivative of formula IV is allowed to react in the presence of a base, for example sodium hydride or potassium tertubtanolate, and an oprotic solvent, for example tetrahydrofuran, with carbon disulfide at temperatures of from 0° C. to 80° C., and immediately afterwards an alkylating agent, for example R₂ -Hal or R₂ OSO₂ OR₂ wherein R₂ is as defined for formula I and Hal is halogen, especially chlorine, bromine or iodine, is added at temperatures of from 0° C. to the reflux temperature of the solvent used.

The compounds of formula XIII in Reaction Scheme 2 can be prepared in accordance with known methods (for example Chem. ber. 92, 2593 (1959) or Acta Chem. Scand. 16, 2395 (1962)), for example by reaction of hydrazine or hydrazine hydrate with carbon disulfide and subsequent alkylation with the reagent R₂ -Hal or R₂ OSO₂ OR₂ wherein R₂ is as defined for formula I and Hal is halogen, especially chlorine or bromine, in the presence of a base. Suitable solvents are, for example, alcohols, for example ethanol, and suitable bases are, for example, alcoholates, for example sodium methanolate or sodium ethanolate, or potassium or sodium hydroxide.

The starting compound of formula IV in Reaction Scheme 4 can be prepared analogously to known procedures, for example in accordance with Methods a), b), c) and d) given in Reaction Scheme 5 below. ##STR24##

In Reaction Scheme 5, the radicals R₁, R₄, R₅ and R₆ are as defined for formula I, it being necessary to note that not all substituent definitions are compatible with all the procedures indicated. The selection of the suitable preparation method is made in accordance with the properties (reactivites) of the substituents in the intermediates in question.

The reaction according to Method a) in Reaction Scheme 5 is carried out analogously to `Vogel's Textbook of Practical Organic Chemistry`, Longman 1989, page 1006 ff. In that reaction the aromatic compound of formula V is allowed to react in the presence of a carboxylic acid derivative, for example a carboxylic acid chloride of formula VI and an acid, for example a Lewis acid such as aluminium chloride, with or without a solvent at temperatures of from 0° C. to 150° C.

The reaction according to Method b) in Reaction Scheme 5 is carried out, for example, starting from the carboxylic acid derivatives of formula Va wherein X₁ is --OH or --N(CH₃)OCH₃ with an alkylithium compound of formula VII or a grignard compound (alkylmagnesium chloride or bromide) of formula VIII in an inert solvent, preferably diethyl ether at temperatures of from -100° C. to 50° C., analogously to Organic Reactions 18, 1 (1970), Organic Synthesis 49, 81 (1969) and `Comprehensive Organic Transformations`, Editor R. C. Larock, VCH 1989, page 685.

The reaction according to Method c) in Reaction Scheme 5 is carried out analogously to `Advanced Organic Chemistry`, Editor J. March, McGraw-Hill Book Company, New York, 1985, pages 816 ff. and 1057 ff., starting from an aldehyde of formula Vc by means of a Grignard reagent of formula VIII, for example alkylmagnesium chloride or bromide, or by means of alkyllithium in an inert solvent, preferably diethyl ether, at temperatures of from -80° C. to 25° C. and subsequent oxidation of the alcohol to the ketone. Suitable oxidising agents are, for example, potassium permanganate, pyridinium dichromate and sodium dichromate.

The reaction according to Method d) in Reaction Scheme 5 is carried out analogously to J. Chem. Soc. 1954, 1297. The amines of formula Vb are accordingly first diazotised to form the corresponding diazonium salts and allowed to react with an aldehydeoxime of formula IX. Subsequent hydrolysis, for example with aqueous sodium acetate and copper sulfate, yields the corresponding methyl ketone of formula IV.

The starting compounds of formulae V, Va, Vb, Vc, VI, VII, VIII, IX and XI in Reaction Schemes 1, Route b), and 5 are known or can be prepared in accordance with known procedures.

The phenylpyrazole derivatives of formula II are novel and have been developed especially for the synthesis of the compounds of formula I. They are therefore also a subject of the present invention.

A large number of known standard procedures is available for the preparation of the phenylpyrazoles of formula I substituted in the 5-position of the phenyl ring (R₆), the selection of the suitable preparation processes being made in accordance with the properties (reactivites) of the substituents in the intermediates in question. Some examples are given in Reaction Schemes 6 to 9.

The preparation of the phenylpyrazole derivatives of formula I that are O-substituted in the 5-position of the phenyl rings, wherein R₆ ═OR₂₀, starting from the methoxy- or benzyloxy-substituted derivatives of formula I₁ or I₂, respectively, is illustrated in Reaction Scheme 6. ##STR25##

The phenolpyrazole derivatives of formula I₃ in Reaction Scheme 6 can be obtained, for example, a) from the compounds of formula I₁ via ether cleavage by means of lithium chloride in N,N-dimethylformamide (DMF) at elevated temperature, as described, for example, in Synthesis 1989, 287, or by means of boron tribromide in dichloromethane at temperatures of from -80° C., to 20° C., as described, for example, in Org. Synth., Collect. Vol. V, 412, 1973; or b) from the compounds of formula I₂ via hydrogenolysis by means of hydrogen in the presence of a catalyst, for example palladium on carbon, as described, for example, in J. Am. Chem. Soc. 93, 746 (1971).

The derivatisation of the phenolpyrazoles of formula I₃ in Reaction Scheme 6 to form the compounds of formula I can be carried out in accordance with standard procedures, for example via alkylation with R₂₀ -Hal wherein R₂₀ is as defined for formula I and Hal is halogen, especially chlorine, bromine or iodine.

The preparation of the phenylpyrazole derivatives of formula I that are S-substituted in the 5-position of the phenyl ring, wherein R₆ ═S(O_(m) R₃₀, starting from the derivatives of formula I₄ that are unsubstituted in the 5-position, is illustrated in Reaction Scheme 7. ##STR26##

The preparation of the thiophenolpyrazoles of formula I₆ in Reaction Scheme 7 can be carried out analogously to known procedures, as described, for example, in J. Org. Chem. 54, 6096 (1989), EP-A-0 259 265 or in "Sulfonation and Related Reactions", Editor Gilbert, Interscience Publishers, New York 1965. The phenylpyrazole of formula I₄ is then chlorosulfonylated with chlorosulfonic acid or sulfur trioxide in sulfuric acid to form the compound of formula I₅ and then reduced with tin chloride or zinc chloride to the thiophenol derivative of formula I₆. The derivatisation of the thiophenolpyrazoles of formula I₆ to form the compounds of formula I in Reaction Scheme 7 can be carried out in accordance with standard procedures, for example via alkylation with R₃₀ -Hal wherein R₃₀ is as defined for formula I and Hal is halogen, especially chlorine, bromine or iodine (m=0). The subsequent oxidation to the sulfine or sulfone derivatives of formula I (m=1 or 2, respectively) can likewise be carried out in accordance with standard procedures, for example with peracids, for example m-chloroperbenzoic acid.

The preparation of the phenylpyrazole derivatives of formula I that are carboxy-substituted in the 5-position of the phenyl ring, wherein R₆ is halogen, cyano, nitro, amino, NHR₁₀, NR₁₀ R₁₁, COR₄₀ or COYR₅₀, starting from the derivatives of formula I₄ or I₁₁ that are unsubstituted in the 5-position or triflate-substituted in the 5-position, respectively, is illustrated in Reaction Scheme 8. ##STR27##

In Reaction Scheme 8, W is the radical ##STR28## wherein R₁ to R₃ and n are as defined for formula I. In accordance with Reaction Scheme 8, the phenylpyrazole of formula I₄ can be converted into an aniline derivative of formula I₈ in accordance with standard procedures, for example nitration in a nitric acid and sulfuric acid mixture and subsequent reduction of the resulting nitro compound of formula I₇ with hydrogen in the presence of a catalyst or according to Bechamps. The aniline derivative of formula I₈ can then be either derivatised directly to form the corresponding compounds of formula I according to standard procedures, for example alkylation or acylation, or converted into the halogen compound of formula I₉ by means of diazotisation and Sandmeyer reaction. The benzoic acid ester of formula I₁₀ in Reaction Scheme 8 can be obtained, for example, analogously to J. Org. Chem. 39, 3318 (1974) or ibid. 40, 532 (1975) from the compound of formula I₉ by means of carbon monoxide and a catalyst, for example palladium chloride-triphenylphosphine (PdCl₂ (TPP)₂) in the presence of a solvent, for example ethanol, optionally under pressure at elevated temperature. A further possible method of preparing the intermediate of formula I₁₀ is carried out analogously to Tetrahedron Letters 25, 2271 (1984) and ibid, 27, 3931 (1986). According to that method, the compound of formula I₁₁ is carbonylated in the presence of a catalyst, for example palladium. The subsequent hydrolysis of the benzoic acid ester of formula I₁₀ yields the benzoic acid derivative of formula I₁₂, which can be converted into the corresponding compounds of formula I in accordance with standard procedures, for example esterification or amidation.

The preparation of the phenylpyrazole derivatives of formula I that are substituted in the 5-position of the phenyl ring, wherein R₆ is C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₂ -C₄ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂, starting from the derivatives of formula I₉ that are substituted in the 5-position of the phenyl ring by halogen, especially by chlorine, bromine or iodine, via Heck reaction (Route a)), or starting from the derivatives of formula I₈ that are substituted in the 5-position of the phenyl ring by amino via diazotisation and subsequent Meerwein reaction, is illustrated in Raction Scheme 9. ##STR29##

In Reaction Scheme 9, W is the radical ##STR30## wherein R₁ to R₃ and n are as defined for formula I. In accordance with Reaction Scheme 9, Route a), the alkynyl ester derivatives of formula I₁₃ can be prepared, for example, via Heck reaction analogously to R. F. Heck in W. G. Dauben (Edit.), Organic Reactions 27, 345 (1982). It is possible to obtain therefrom by means of standard procedures, for example by means of partial or complete hydrogenation, the corresponding alkenyl- or alky-COZR₅₂ derivatives, respectively, or via halogenation the corresponding haloalkenyl- or haloalkyl-COZR₅₂ derivatives of formula I.

In accordance with Reaction Scheme 9, Route b), the haloalkylCOZR₅₂ derivatives of formula I₁₄ can be produced from the aniline derivatives of formula I₈ analogously to Organic Reactions 11, 189-260 (1960) via diazotisation and Meerwein reaction. Known standard procedures, for example hydrogenolysis or halogen removal, yield therefrom the corresponding alkyl- or alkenyl-COZR₅₂ derivatives of formula I. ##STR31##

The formation of the pyrazole rings of the compounds of formula I according to Reaction Scheme 10 is carried out

a) starting from the ketone derivative of formula IV wherein R₁ and R₄ to R₆ are as defined for formula I, by reaction with a carbonate of formula XVI wherein R₇ is C₁ -C₄ alkyl, phenyl or benzyl, in the presence of a base, especially the corresponding sodium alcoholate R₇ O⁻⁺ Na, in a solvent, for example the corresponding alcohol R₇ OH together with a second solvent, for example an ether or hydrocarbon, at temperatures of from 0° C. to the boiling point of the solvent in question, or

b) starting from the α-haloketone of formula XII wherein R₁ and R₄ to R₆ are as defined and Hal is halogen, especially chlorine or bromine, by carbonylation in the presence of the palladium(II) chloride-bis-triphenylphosphine complex PdCl₂ [(PH)₃ P]₂ as catalyst, carbon monoxide and a phase transfer catalyst in a suitable solvent, for example the alcohol R₇ OH wherein R₇ is as defined, together with a second solvent, for example N,N-di-methylformamide, analogously to Indian J. Chem. B 31,363 (1982).

In Reaction Scheme 10 the preparation of the pyrazolinone rings of formula XVII that are unsubstituted at the nitrogen atom is carried out by reaction of the above-prepared keto ester of formula XVI with hydrazine or hydrazine hydrate optionally in the presence of a suitable solvent at elevated temperature, preferably hydrazine hydrate in alcoholic solution at elevated temperature.

For the preparation of the pyrazolinone rings of formula XVIII that are substituted at the nitrogen atom, the reagent used is the compound of formula XI, for example N-alkyl-hydrazine, preferably N-methylhydrazine.

If desired, the substituted pyrazolinone derivative of formula XVIII can be prepared also via N-alkylation of the corresponding unsubstituted pyrazolinones of formula XVII, in a manner analogous to that described in Reaction Scheme 3.

The conversion of the pyrazolinone derivatives of formula XVIII into the corresponding mercapto analogues of formula XV is carried out in accordance with standard methods, for example with the aid of Lawesson reagent in a suitable solvent at elevated temperatures. The subsequent S-alkylation yields compounds of formula I (n=0) and is carried out in accordance with standard methods with the aid of an alkylating agent, for example R₂ -Hal wherein R₂ is as defined for formula I and Hal is halogen, especially chlorine or bromine, optionally in the presence of a solvent and a base.

The compounds of formula XV are novel and have been developed especially for the synthesis of the compounds of formula I. They are therefore also a subject of the present invention.

All further compounds originating from the scope of formula I can easily be prepared from the described compounds of formula I in manner analogous to that described above, or in accordance with methods as described, for example, in "Methoden der Organischen Chemie" (Houben-Weyl), Volume E 8b, Georg Thieme Verlag Stuttgart, 1994, page 399 ff. or in "Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings", Editor R. H. Wiley, Interscience Publishers, New York, 1967, page 1 ff., or by derivatisation in accordance with known standard methods, for example alkylation, acylation and amidation.

The end products of formula I can be isolated in customary manner by concentration and/or evaporation of the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography or flash column chromatography and a suitable eluant.

For the use according to the invention of the compounds of formula I, or compositions comprising them, there come into consideration all the methods of application customary in agriculture, for example pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques, for example the controlled release of active ingredient. For that purpose a solution of the active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. If required, it is also possible to apply a coating (coated granules) which allows the active ingredient to be released in metered amounts over a specific period of time.

The compounds of formula I may be used in unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants customarily employed in formulation technology e.g. into emulsifiable concentrates, directly sprayable or diutable solution, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I or at least one compound of formula I and generally one or more solid or liquid formulation adjuvants, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, e.g. solvents or solid carriers. It is also possible to use surface-active compounds (surfactants) in the preparation of the formulations.

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, such as mixtures of alkylbenzens, e.g. xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons, such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol; glycols and their ethers and esters, such as propylene glycol or dipropylene glycol ether; ketones, such as cyclohexanone, isophorone or diacetone alcohol; strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water, vegetable oils and esters thereof, such as rape oil, castor oil or soybean oil; and, where appropriate, also silicone oils.

The solid carriers used, e.g. for dusts and dispersible powders, are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite, and suitable nonsorbent carriers are, for example, calcite or sand. In addition, a great numer of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.

Depending upon the nature of the compound of formula I to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Both water-soluble soaps and water-soluble synthetic surface-active compounds are suitable anionic surfactants.

Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurin salts.

More frequently, however, so-called synthetic surfactants are used, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a C₈ -C₂₂ alkyl radical, which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt or lignosulfonic acid, of dodecyl sulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde.

Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per rpopylene glycol unit.

Examples of non-ionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, e.g. pollyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in formulation technology, which may also be used in the compositions according to the invention, are described inter alia in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., 1981; Stache, H., "Tensid-Taschenbuch" (Surfactant Handbook), Carl Hanser Verlag, Munich/Vienna 1981; and M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-1981.

The herbicidal compositions usually comprise 0.1 to 99%, preferably 0.1 to 95%, of a compound of formula I, 1 to 99.9% of a solid or liquid formulation adjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The compositions may also comprise further auxiliaries, such as stabilisers, e.g. vegetable oils or expoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients.

Preferred formulations have especially the following compositions (throughout, percentages are by weight):

Emulsifiable concentrates:

active ingredient: 1 to 90%, preferably 5 to 50%

surface-active agent: 5 to 30%, preferably 10 to 20%

solvent: 15 to 94%, preferably 70 to 85%

Dusts:

active ingredient: 0.1 to 50%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates:

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 24%, preferably 88 to 30%

surface-active agent: 1 to 40%, preferably 2 to 30%

Wettable powders:

active ingredient: 0.5 to 90%, preferably 1 to 80%

surface-active agent: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%

Granules:

active ingredient: 0.1 to 30%, preferably 0.1 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%

The compounds of formula I are generally used successfully when applied to the plant or to the locus thereof at rates of application of from 0.001 to 2 kg/ha, especially from 0.005 to 1 kg/ha. The concentration required to achieve the desired effect can be determined by experiment. It is dependent upon the type of action, the stage of development of the cultivated plant and of the weed, and also upon the application (place, time, method) and, in dependence on those parameters, can vary within wide limits.

The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties which render them suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control.

Crops are also to be understood as being those which have been rendered tolerant to herbicides or classes of herbicide byu conventional methods of breeding or genetic engineering.

The following Examples further illustrate, but do not limit, the invention.

PREPARATION EXAMPLES Example P1: 1-(2,4-Dichlorophenyl)-3,3-bis(methylthio)-2-methyl-2-propen-1-one ##STR32##

1.07 g (0.005 mol) of 1-(2,4-dichlorophenyl)-1-propanone (95%) are added to an emulsion of 0.24 g (0.01 mol) of sodium hydride in 8 ml of dry tetrahydrofuran and the mixture is stirred at 40° C. for one hour. The reaction mixture is cooled to 0° C. and 0.381 g (0.05 mol) of carbon disulfide is added at 0-5° C. Immediately after the addition of carbon disulfide is complete, 1.42 g (0.01 mol) of methyl iodide are added dropwise at 0-5° C. and the reaction mixture is stirred for one hour, then poured into 25 ml of a mixture of ice/water and stirred for a further 30 minutes. The crude produce is extracted with ether and the organic phase is separated off, dried over sodium sulfate and concentrated by evaporation. The resulting residue is purified by column chromatography using 10% ethyl acetate in hexane as eluant. The desired product is obtained in a yield of 1.38 g (89.8%) in the form of a yellow oil.

Example P2: 3-(2,4-Dichlorophenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR33##

0.138 g (0.003 mol) of methyl hydrazine is added to a solution of 0.614 g (0.002 mol) of 1-(2,4-dichlorophenyl)-3,3-bis(methylthio)-2-methyl-2-propen-1-one in 10 ml of acetonitrile and the reaction mixture is heated at 80° C. for 8 hours. The mixture is then concentrated in vacuo and the residue is taken up in ether, washed with water and dried over sodium sulfate. After the ether phase has been concentrated by evaporation, the residue is purified by column chromatography over silica gel with hexane/ethyl acetate 2/1 as eluant. The desired product is obtained in a yield of 0.425 g (74.0%) in the form of a white solid having a melting point of 65-66° C. (recrystallised from hexane).

Example P3: 3-(2,4-Dichlorophenyl)-4-methyl-5-(methylsulfonyl)-1-methyl-[1H]-pyrazole ##STR34##

0.515 g (0.0015 mol) of m-chloroperbenzoic acid (50-60%) is added to a solution of 0.214 g (0.00075 mol) of 3-(2,4-dichlorophenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole in 10 ml of dichlormethane and the reaction mixture is stirred at 22° C. overnight. The mixture is then washed with a saturated sodium hydrogen carbonate solution that contains 5% sodium thiosulfate and then with water, dried over sodium sulfate and concentrated by evaporation. The resulting residue is purified by column chromatography over silica gel with hexane/ethyl acetate 1/1. The desired product is obtained in a yield of 0.206 g (86.2%) in the form of a white solid having a melting point of 110-112° C.

Example P4: 3-(4-Chloro-2-fluorophenyl)-4-methyl-5-(methylthio)-[1H]-pyrazole ##STR35##

0.6 ml (0.01 mol) of carbon disulfide in 2 ml of ethanol is added dropwise at 20-28° C. to 3.35 ml (0.01 mol) of a 21% ethanolic sodium ethanolate solution and 0.49 ml (0.01 mol) of hydrazine hydrate in 10 ml of ethanol. After 0.5 hour's stirring at 22° C., 0.62 ml (0.01 mol) of methyl iodide is added dropwise at 20-22° C. to the suspension that has formed. After 1 hour's stirring at 22° C., 3.35 ml (0.01 mol) of 21% ethanolic sodium ethanolate solution are added to the resulting suspension and stirring is continued for a further 10 minutes. The resulting solution is then cooled to 5-10° C. and 2.7 g (0.01 mol) of α-bromo-4-chloro-2-fluoropropiophenone in 5 ml of ethanol are added dropwise to the solution and stirring is continued for a further 10 minutes at 40-45° C. 10 ml of 2N hydrochloric acid are added dropwise at 22° C. to the solution that has formed and stirring is continued for 1 hour at 22° C. and then for 15 minutes at 40-45° C. The resulting suspension is dissolved in tert-butyl methyl ether, washed three times with water and concentrated by evaporation using a rotary evaporator. As residue there is obtained 2.5 g of an oil which is chromatographed over 50 g of silica gel with ethyl acetate/hexane 1/2 as eluant. 1.4 g (54.6%) of the desired compound are obtained in the form of colourless crystals having a melting point of 88-90° C.

Example P5: α-Bromo-4-chloro-2-fluoropropiophenone ##STR36##

2.2 ml (0.42 mol) of bromine are added dropwise at 20-25° C. to a solution of 8.5 g (0.04 mol) of 4-chloro-2-fluoropropiophenone and 0.1 ml of 33% hydrobromic acid in 20 ml of acetic acid. After being stirred for 1 hour at 22° C., the mixture is poured into ice-water, extracted with tert-butyl methyl ether and washed neutral with dilute sodium hydrogen carbonate solution. The reaction mixture is then concentrated by evaporation using a rotary evaporator and then dried at 22° C. for 1 hour under a high vacuum. 10.4 g of 95% α-bromo-4-chloro-2-fluoropropiophenone and obtained in the form of a light-yellow oil.

Example P6: α-Bromo-4-chloro-2-fluoro-5-methoxypropiophenone ##STR37##

54 ml (1.05 mol) of bromine are added dropwise at 20-25° C. to a suspension of 217 g (1 mol) of 4-chloro-2-fluoro-5-methoxypropiophenone and 10 ml of 33% hydrobromic acid in glacial acetic acid in 0.5 liter of acetic acid. After being stirred for 1 hour to complete the reaction, the solution that has formed is poured into 2 liters of ice-water, extracted with tert-butyl methyl ether (MTBE), washed four times with water, dried over magnesium sulfate and concentrated by evaporation. 284 g of the desired compound are obtained in the form of a 95% oil.

Example P7: 3-(4-Chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-(methylthio)-[1H]-pyrazole ##STR38##

At 0-5° C., 37 g (0.3 mol) of methyl dithiocarbazate are added in portions to a solution of 120 ml (0.32 mol) of 21% sodium ethanolate solution in ethanol. 95 g (0.3 mol) of α-bromo-4-chloro-2-fluoro-5-methoxypropiophenone (90%) are added dropwise at -5-0° C. to the resulting solution. After being stirred for 30 minutes at 0-5° C., the suspension that has formed is diluted with 250 ml of ethanol and stirred at 0-5° C. for a further 2 hours. Then, after 1 hour's stirring at 22° C., 25 ml of 37% hydrochloric acid are added dropwise at 25-30° C. and stirring is continued for a further 3 hours. Then 30 ml of 30% sodium hydroxide solution are added dropwise and the resulting mixture is concentrated by evaporation. After the addition of about 1 liter of tert-butyl methyl ether, the reaction mixture is washed with water and the organic phase is dried and concentrated by evaporation. The crude product is purified by silica gel chromatography. 60 g (70% of the theoretical yield) of the desired compound are obtained in the form of brown crystals having a melting point of 95-100° C.

Example P8: 3-(4-Chloro-2-fluorophenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR39##

1.4 ml (0.022 mol) of methyl iodide are added to a mixture of 5.4 g (0.02 mol) of 3-(4-chloro-2-fluorophenyl)-4-methyl-5-(methyllthio)-[1H]-pyrazole (Example P4) and 4.2 g (0.030 mol) of potassium carbonate in 25 ml of 1-methyl-2-pyrrolidone (NMP). After stirring overnight at 22° C., approximately 200 ml of tert-butyl methyl ether (MTBE) are added, and the mixture is washed three times with water and concentrated by evaporation. The crude product is purified by means of silica gel chromatography. 3.2 g (59% of the theoretical yield) of the desired compound are obtained in the form of an oil.

Example P9: 3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR40##

A mixture of 15 g (0.05 mol) of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P7) and 10.6 g (0.25 mol) of lithium chloride in 100 ml of N,N-dimethylformamide is stirred at 22° C. in an argon atomsphere for 2.5 days. The solution is cooled and poured into 0.5 liter of ice-water and 15 ml of 37% hydrochloric acid and extracted with tert-butyl methyl ether (MTBE). The organic phase is extracted with a dilute sodium hydroxide solution, and the aqueous phase is separated off and again acidified and extracted with MTBE. AFter concentration by evaporation and recrystallisation in diethyl ether, 4.8 g (33.5% of the threoretical yield) of the desired product are obtained in the form of crystals having a melting point of 136-138° C. and 7.6 g of crude product of the desired compound in the form of an oil.

Example P10: 3-(4-Chloro-2-fluoro-5-trifluoromethylsulfonyloxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR41##

65 ml (0.8 mol) of pyridine and then 80 ml (0.48 mol) of trifluoromethanesulfonic acid anhydride are added dropwise at 0-5° C. to a solution of 129 g (0.3 mol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (approx. 70%) (Example P9) in 1.2 liters of 1,4-dioxane. After being stirred for 30 minutes at 0-5° C. and then at 22° C. overnight, the reaction mixture is concentrated to approximately 1/3 of its original volume by evaporation, poured into a mixture of ice, water and hydrochloric acid, extracted with MTBE, washed with water and concentrated by evaporation. After purification of the crude product by silica gel chromatography, 87.7 g (70% of the theoretical yield) of the desired compound are isolated in the form of crystals having a melting point of 54-56° C.

Example P11: 3-(4-Chloro-2-fluoro-5-methoxycarbonylphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR42##

A mixture of 40.7 g (0.1 mol) of 3-(4-chloro-2-fluoro-5-trifluoromethylsulfonyloxyphenyl)-4-methyl-5(methylthio)-1-methyl-[1H]-pyrazole (Example P10), 31 ml (0.22 mol) of triethylamine, 1.12 g (0.005 mol) of palladium(II) acetate and 2.06 g (0.005 mol) of 1,3-bis(diphenylphosphino)propane (Ph₂ P(CH₂)₃ PPh₂) in 300 ml of N,N-dimethylformamide and 215 ml of methanol is stirred at 70° C. at a pressure of 5 bar of carbon monoxide for 2 hours. The solution is then concentrated by evaporation, the resulting residue is dissolved in tert-butyl methyl ether (MTBE), washed with 0.2N hydrochloric acid and water, concentrated by evaporation and purified by means of silica gel column chromatography. 23.4 g (71.3% of the theoretical yield) of the desired compound are obtained in the form of crystals having a melting point of 82-83° C.

Example P12: 3-(4-Chloro-2-fluoro-5-proparglyoxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole ##STR43##

1 ml (0.0132 mol) of propargyl bromide are added dropwise at 20-25° C. to a mixture of 3.15 g (0.011 mol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P9) and 2.5 g (0.018 mol) of potassium carbonate in 30 ml of N,N-dimethylformamide. After being stirred for 18 hours at 22° C., the mixture is poured into water, extracted with tert-butyl methyl ether (MTBE), washed with water and concentrated by evaporation. After recrystallisation in petroleium ether, 2.84 g (81.1% of the theoretical yield) of the desired compound are obtained in the form of crystals having a melting point of 76-78° C.

Example P13: 3-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-(methylsulfinyl)-1-methyl-[1H]-pyrazole ##STR44##

A solution of 1.57 g (0.005 mol) of 50-60% 3-chloroperbenzoic acid in 30 ml of dichloromethane is added dropwise at 0-5° C. to a solution of 1.7 g (0.005 mol) of 3-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P12) in 20 ml of dichloromethane. After being stirred overnight at 22° C., the reaction mixture is washed with a dilute sodium hydrogen carbonate solution, then with water and concentrated by evaporation, and the resulting residue is recrystallised in petroleum ether/diethyl ether. 1.5 g (88.2% of the theoretical yield) of the desired compound are isolated in the form of crystals having a melting point of 93-96° C.

Example P14: 3-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-(methylsulfonyl)-1-methyl-[1H]-pyrazole ##STR45##

A solution of 3.45 g (0.011 mol) of 50-60% 3-chlroperbenzoic acid in 60 ml of dichlormethane is added dropwise at 0-5° C. to a solution of 1.7 g (0.005 mol) of 3-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-(methylthio)-1-methyl-[1H]-pyrazole (Example P12) in 20 ml of dichloromethane. After being stirred overnight at 22° C., the reaction mixture is washed with a dilute sodium hydrogen carbonate solution, then with water and concentrated by evaporation, and the resulting residue is recrystallised in diethyl ether. 1.4 g (78.6% of the theoretical yield) of the desired compound are obtained in the form of crystals having a melting point of 123-124° C.

In an analogous manner or by means of known methods it is also possible to prepare the compounds listed in the Tables which follow.

                  TABLE 1                                                          ______________________________________                                         Compounds of formula Ia                                                                                      (Ia)                                              ##STR46##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         1.1        H                  oil                                              1.2        NH.sub.2           55-60                                            1.3        NO.sub.2                                                            1.4        Br                                                                  1.5        I                                                                   1.6        CN                                                                  1.7        OCH.sub.3          64-70                                            1.8        N(SO.sub.2 CH.sub.3).sub.2                                          1.9        NHSO.sub.2 CH.sub.3                                                                               142-144                                          1.10       OC.sub.3 H.sub.7 (iso)                                                                            oil                                              1.11       O-propargyl        72-75                                            1.12       OCH(CH.sub.3)C.tbd.CH                                                                             oil                                              1.13       O-phenyl                                                            1.14       O-2-pyridyl                                                         1.15       O-2-pyrimidinyl                                                     1.16       OCH.sub.2 COOCH.sub.2 CH.sub.3                                                                    95-97                                            1.17       OCH.sub.2 CH.sub.2 OCH.sub.3                                        1.18       OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                               1.19       OCH.sub.2 COOCH.sub.3                                               1.20       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                   1.21       OCH.sub.2 COO-benzyl                                                1.22       OCH(CH.sub.3)COObenzyl (S)                                          1.23       OCH(CH.sub.3)COObenzyl (R)                                          1.24       OCH(CH.sub.3)COObenzyl (R,S)                                        1.25       SC.sub.3 H.sub.7 (iso)                                              1.26       SH                 solid                                            1.27       SCH.sub.2 COOCH.sub.3                                                                             oil                                              1.28       SCH.sub.2 COOC.sub.2 H.sub.5                                        1.29       SCH(CH.sub.3)COObenzyl (S)                                          1.30       SCH(CH.sub.3)COObenzyl (R)                                          1.31       SCH(CH.sub.3)COObenzyl (R,S)                                        1.32       SCH.sub.2 COObenzyl                                                 1.33       SO.sub.2 Cl        solid                                            1.34       SO.sub.2 CH.sub.3                                                   1.35       SO.sub.2 NHCH.sub.3                                                 1.36       COOH               177-179                                          1.37       COOCH.sub.3        82-83                                            1.38       COOC.sub.3 H.sub.7 (iso)                                                                          oil                                              1.39       COOC(CH.sub.3).sub.2 COOH                                                                         amorphous                                        1.40       COOC(CH.sub.3).sub.2 COO-allyl                                                                    oil                                              1.41       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    1.42       COOC(CH.sub.3).sub.2 COOethyl                                                                     72-75                                            1.43       COOC(CH.sub.3).sub.2 CONH-allyl                                     1.44       CH.sub.2 CHClCOOethyl                                                                             oil                                              1.45       CH.sub.2 CH═CH.sub.2                                                                          oil                                              1.46       CH.sub.2 CH.sub.2 CH.sub.3                                          1.47       CH.sub.2 CH.sub.2 CF.sub.3                                          1.48       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 1.49       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 1.50       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                                             oil                                              1.51       CH.sub.2 CHClCOOH  170-172                                          1.52       CH.sub.2 CHClCOOCH.sub.3                                            1.53       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               1.54       CH.sub.2 CHClCONHallyl                                              1.55       CH.sub.2 C(CH.sub.3)ClCOOH                                          1.56       CH.sub.2 C(CH.sub.3)ClCOOC.sub.2 H.sub.5                                                          oil                                              1.57       CH.sub.2 C(CH.sub.3)ClCOOEt                                         1.58       CH.sub.2 C(CH.sub.3)ClCONHEt                                        1.59       CH.sub.2 CH.sub.2 COOH                                              1.60       CH.sub.2 CH.sub.2 COOCH.sub.3                                       1.61       CH.sub.2 CH.sub.2 COOEt                                             1.62       CHClCHClCOOH                                                        1.63       CHClCHClCOOCH.sub.3                                                 1.64       CHClCHClCOOEt                                                       1.65       CH.sub.2 CH(OCH.sub.3)COOH                                          1.66       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   1.67       CH.sub.2 CH(OCH.sub.3)COOEt                                         1.68       CH.sub.2 CH(SCH.sub.3)COOH                                          1.69       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   1.70       CH.sub.2 CH(SCH.sub.3)COOEt                                                                       oil                                              1.71       CH═CHCOOH                                                       1.72       CH═CHCOOCH.sub.3                                                1.73       CH═CHCOOEt                                                      1.74       CH═CClCOOH                                                      1.75       CH═CClCOOCH.sub.3                                               1.76       COOEt                                                               1.77       CONH.sub.2                                                          1.78                                                                                       ##STR47##         55-57                                            1.79       CONHSO.sub.2 CH.sub.3                                               1.80       COOCH.sub.2 COOH                                                    1.81       COOCH.sub.2 COOCH.sub.3                                             1.82       COOCH(CH.sub.3)COOH                                                 1.83       COOCH(CH.sub.3)COOCH.sub.3                                          1.84       COOCH(CH.sub.3)CH.sub.2 COOH                                        1.85       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 1.86       COOC(CH.sub.3).sub.2 CN                                             1.87       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      1.88       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 1.89                                                                                       ##STR48##         59-62                                            1.90       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                                                           oil                                              1.91       COOCH.sub.2 C.tbd.CH                                                1.92       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           1.93       COOCH(CH.sub.3)C.tbd.CH                                             1.94       COOC(CH.sub.3).sub.2 COCH.sub.3                                     1.95       NHallyl                                                             1.96       N(COCH.sub.3)allyl                                                  1.97       N(Et)SO.sub.2 CH.sub.3                                              1.98       N(allyl)SO.sub.2 CH.sub.3                                                                         83-85                                            1.99       N(allyl)SO.sub.2 Et                                                                               65-68                                            1.100      SO.sub.2 N(CH.sub.3).sub.2                                          1.101      SO.sub.2 NH.sub.2                                                   1.102      SO.sub.2 NHCOCH.sub.3                                               1.103      OH                 oil                                              1.104      OEt                                                                 1.105      Oallyl                                                              1.106      OCH.sub.2 C.tbd.CCH.sub.3                                           1.107      OCH(CH.sub.3)CH═CH.sub.2                                        1.108      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               1.109      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                                                   oil                                              1.110                                                                                      ##STR49##         86-89                                            1.111      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       1.112      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            1.113      OCH.sub.2 CH.sub.2 COOH                                             1.114      OC(CH.sub.3).sub.2 COOH                                             1.115      OC(CH.sub.3).sub.2 COOCH.sub.3                                      1.116      OC(CH.sub.3).sub.2 COOEt                                            1.117      OCH.sub.2 COOH                                                      1.118      OSO.sub.2 CH.sub.3                                                  1.119      OSO.sub.2 CF.sub.3 54-56                                            1.120      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     1.121      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             1.122      CH.sub.2 CHClCONHOH                                                 1.123      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            1.124      CH.sub.2 CH(CH.sub.3)COOH                                           1.125      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             1.126                                                                                      ##STR50##                                                          1.127      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          1.128                                                                                      ##STR51##                                                          1.129      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          1.130      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   1.131                                                                                      ##STR52##         91-93                                            1.132      NHSO.sub.2 C.sub.2 H.sub.5                                                                        121-124                                          1.133      NHCH.sub.2 C.tbd.CH                                                                               103-105                                          ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                         Compounds of formula Ib                                                                                      (Ib)                                              ##STR53##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         2.1        H                  113-115                                          2.2        NH.sub.2           solid                                            2.3        NO.sub.2           128-130                                          2.4        Br                                                                  2.5        I                                                                   2.6        CN                                                                  2.7        OCH.sub.3          89-92                                            2.8        N(SO.sub.2 CH.sub.3).sub.2                                          2.9        NHSO.sub.2 CH.sub.3                                                 2.10       OC.sub.3 H.sub.7 (iso)                                                                            oil                                              2.11       O-propargyl        93-96                                            2.12       OCH(CH.sub.3)C.tbd.CH                                                                             resin                                            2.13       O-phenyl                                                            2.14       O-2-pyridyl                                                         2.15       O-2-pyrimidinyl                                                     2.16       OCH.sub.2 COOC.sub.2 H.sub.5                                                                      95-98                                            2.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                   2.18       OCH.sub.2 COO-benzyl                                                2.19       OCH(CH.sub.3)COObenzyl (S)                                          2.20       OCH(CH.sub.3)COObenzyl (R)                                          2.21       OCH(CH.sub.3)COObenzyl (R,S)                                        2.22       SC.sub.3 H.sub.7 (iso)                                              2.23       SH                                                                  2.24       SCH.sub.2 COOCH.sub.3                                               2.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        2.26       SCH(CH.sub.3)COObenzyl (S)                                          2.27       SCH(CH.sub.3)COObenzyl (R)                                          2.28       SCH(CH.sub.3)COObenzyl (R,S)                                        2.29       SCH.sub.2 COObenzyl                                                 2.30       SO.sub.2 Cl                                                         2.31       SO.sub.2 CH.sub.3                                                   2.32       SO.sub.2 NHCH.sub.3                                                 2.33       COOH               138-164                                          2.34       COOCH.sub.3        oil                                              2.35       COOC.sub.3 H.sub.7 (iso)                                                                          oil                                              2.36       COOC(CH.sub.3).sub.2 COOH                                                                         153-166                                          2.37       COOC(CH.sub.3).sub.2 COO-allyl                                                                    oil                                              2.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    2.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     oil                                              2.40       COOC(CH.sub.3).sub.2 CONH-allyl                                     2.41       CH.sub.2 CHClCOOethyl                                                                             resin                                            2.42       CH.sub.2 CH═CH.sub.2                                                                           99-101                                          2.43       CH.sub.2 CH.sub.2 CH.sub.3                                          2.44       CH.sub.2 CH.sub.2 CF.sub.3                                          2.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 2.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 2.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                                             oil                                              2.48       CH.sub.2 CHClCOOH                                                   2.49       CH.sub.2 CHClCOOCH.sub.3                                            2.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               2.51       CH.sub.2 CHClCONHallyl                                              2.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          2.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                   2.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                                                       oil                                              2.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        2.56       CH.sub.2 CH.sub.2 COOH                                              2.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                       2.58       CH.sub.2 CH.sub.2 COOEt                                             2.59       CHClCHClCOOH                                                        2.60       CHClCHClCOOCH.sub.3                                                 2.61       CHClCHClCOOEt                                                       2.62       CH.sub.2 CH(OCH.sub.3)COOH                                          2.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   2.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         2.65       CH.sub.2 CH(SCH.sub.3)COOH                                          2.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   2.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         2.68       CH═CHCOOH                                                       2.69       CH═CHCOOCH.sub.3                                                2.70       CH═CHCOOEt                                                      2.71       CH═CClCOOH                                                      2.72       CH═CClCOOCH.sub.3                                               2.73       COOEt                                                               2.74       CONH.sub.2                                                          2.75                                                                                       ##STR54##         68-71                                            2.76       CONHSO.sub.2 CH.sub.3                                               2.77       COOCH.sub.2 COOH                                                    2.78       COOCH.sub.2 COOCH.sub.3                                             2.79       COOCH(CH.sub.3)COOH                                                 2.80       COOCH(CH.sub.3)COOCH.sub.3                                          2.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        2.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 2.83       COOC(CH.sub.3).sub.2 CN                                             2.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      2.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 2.86                                                                                       ##STR55##                                                          2.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                                                           91-93                                            2.88       COOCH.sub.2 C.tbd.CH                                                2.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           2.90       COOCH(CH.sub.3)C.tbd.CH                                             2.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     2.92       NHallyl                                                             2.93       N(COCH.sub.3)allyl                                                  2.94       N(Et)SO.sub.2 CH.sub.3                                              2.95       N(allyl(SO.sub.2 CH.sub.3                                                                         133-136                                          2.96       N(allyl)SO.sub.2 Et                                                                               solid                                            2.97       SO.sub.2 N(CH.sub.3).sub.2                                          2.98       SO.sub.2 NH.sub.2                                                   2.99       SO.sub.2 NHCOCH.sub.3                                               2.100      OH                                                                  2.101      OEt                                                                 2.102      Oallyl                                                              2.103      OCH.sub.2 C.tbd.CCH.sub.3                                           2.104      OCH(CH.sub.3)CH═CH.sub.2                                        2.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               2.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                                                   oil                                              2.107                                                                                      ##STR56##         96-99                                            2.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       2.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            2.110      OCH.sub.2 CH.sub.2 COOH                                             2.111      OC(CH.sub.3).sub.2 COOH                                             2.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      2.113      OC(CH.sub.3).sub.2 COOEt                                            2.114      OCH.sub.2 COOH                                                      2.115      OSO.sub.2 CH.sub.3                                                  2.116      OSO.sub.2 CF.sub.3                                                  2.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     2.118      CH.sub.2 CHClCON(C.sub.2 H.sub.6).sub.2                             2.119      CH.sub.2 CHClCONHOH                                                 2.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            2.121      CH.sub.2 CH(CH.sub.3)COOH                                           2.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             2.123                                                                                      ##STR57##                                                          2.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          2.125                                                                                      ##STR58##                                                          2.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          2.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   2.128                                                                                      ##STR59##         96-98                                            ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                         Compounds of formula Ic                                                                                      (Ic)                                              ##STR60##                                                                     Comp. No.  R.sub.6            M.p                                              ______________________________________                                         3.1        H                  113-115                                          3.2        NH.sub.2                                                            3.3        NO.sub.2                                                            3.4        Br                                                                  3.5        I                                                                   3.6        CN                                                                  3.7        OCH.sub.3          146-149                                          3.8        N(SO.sub.2 CH.sub.3).sub.2                                          3.9        NHSO.sub.2 CH.sub.3                                                                               199-201                                          3.10       OC.sub.3 H.sub.7 (iso)                                                                            100-103                                          3.11       O-propargyl        123-124                                          3.12       OCH(CH.sub.3)C.tbd.CH                                                                             oil                                              3.13       O-phenyl                                                            3.14       O-2-pyridyl                                                         3.15       O-2-pyrimidinyl                                                     3.16       OCH.sub.2 COOC.sub.2 H.sub.5                                                                      123-126                                          3.17       OCH.sub.2 COOCH.sub.3                                               3.18       OCH.sub.2 COO-benzyl                                                3.19       OCH(CH.sub.3)COObenzyl (S)                                          3.20       OCH(CH.sub.3)COObenzyl (R)                                          3.21       OCH(CH.sub.3)COObenzyl (R,S)                                        3.22       SC.sub.3 H.sub.7 (iso)                                              3.23       SH                                                                  3.24       SCH.sub.2 COOCH.sub.3                                               3.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        3.26       SCH(CH.sub.3)COObenzyl (S)                                          3.27       SCH(CH.sub.3)COObenzyl (R)                                          3.28       SCH(CH.sub.3)COObenzyl (R,S)                                        3.29       SCH.sub.2 COObenzyl                                                 3.30       SO.sub.2 Cl                                                         3.31       SO.sub.2 CH.sub.3                                                   3.32       SO.sub.2 NHCH.sub.3                                                 3.33       COOH               237-240                                          3.34       COOCH.sub.3        94-96                                            3.35       COOC.sub.3 H.sub.7 (iso)                                                                          92-94                                            3.36       COOC(CH.sub.3).sub.2 COOH                                                                         167-169                                          3.37       COOC(CH.sub.3).sub.2 COO-allyl                                                                    oil                                              3.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    3.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     oil                                              3.40       COOC(CH.sub.3).sub.2 CONH-allyl                                     3.41       CH.sub.2 CHClCOOethyl                                                                             resin                                            3.42       CH.sub.2 CH═CH.sub.2                                                                           98-100                                          3.43       CH.sub.2 CH.sub.2 CH.sub.3                                          3.44       CH.sub.2 CH.sub.2 CF.sub.3                                          3.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 3.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 3.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                                             oil                                              3.48       CH.sub.2 CHClCOOH                                                   3.49       CH.sub.2 CHClCOOCH.sub.3                                            3.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               3.51       CH.sub.2 CHClCONHallyl                                              3.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          3.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                   3.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                                                       oil                                              3.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        3.56       CH.sub.2 CH.sub.2 COOH                                              3.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                       3.58       CH.sub.2 CH.sub.2 COOEt                                             3.59       CHClCHClCOOH                                                        3.60       CHClCHClCOOCH.sub.3                                                 3.61       CHClCHClCOOEt                                                       3.62       CH.sub.2 CH(OCH.sub.3)COOH                                          3.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   3.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         3.65       CH.sub.2 CH(SCH.sub.3)COOH                                          3.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   3.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         3.68       CH═CHCOOH                                                       3.69       CH═CHCOOCH.sub.3                                                3.70       CH═CHCOOEt                                                      3.71       CH═CClCOOH                                                      3.72       CH═CClCOOCH.sub.3                                               3.73       COOEt                                                               3.74       CONH.sub.2                                                          3.75                                                                                       ##STR61##         110-112                                          3.76       CONHSO.sub.2 CH.sub.3                                               3.77       COOCH.sub.2 COOH                                                    3.78       COOCH.sub.2 COOCH.sub.3                                             3.79       COOCH(CH.sub.3)COOH                                                 3.80       COOCH(CH.sub.3)COOCH.sub.2                                          3.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        3.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 3.83       COOC(CH.sub.3).sub.2 CN                                             3.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      3.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 3.86                                                                                       ##STR62##         oil                                              3.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                                                           83-86                                            3.88       COOCH.sub.2 C.tbd.CH                                                3.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           3.90       COOCH(CH.sub.3)C.tbd.CH                                             3.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     3.92       NHallyl                                                             3.93       N(COCH.sub.3)allyl                                                  3.94       N(Et)SO.sub.2 CH.sub.3                                              3.95       N(allyl)SO.sub.2 CH.sub.3                                                                         120-122                                          3.96       N(allyl)SO.sub.2 Et                                                                               105-107                                          3.97       SO.sub.2 N(CH.sub.3).sub.2                                          3.98       SO.sub.2 NH.sub.2                                                   3.99       SO.sub.2 NHCOCH.sub.3                                               3.100      OH                                                                  3.101      OEt                                                                 3.102      Oallyl                                                              3.103      OCH.sub.2 C.tbd.CCH.sub.3                                           3.104      OCH(CH.sub.3)C═CH.sub.2                                         3.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               3.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                                                   51-55                                            3.107                                                                                      ##STR63##         125-127                                          3.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       3.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            3.110      OCH.sub.2 CH.sub.2 COOH                                             3.111      OC(CH.sub.3).sub.2 COOH                                             3.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      3.113      OC(CH.sub.3).sub.2 COOEt                                            3.114      OCH.sub.2 COOH                                                      3.115      OSO.sub.2 CH.sub.3                                                  3.116      OSO.sub.2 CF.sub.3                                                  3.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     3.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             3.119      CH.sub.2 CHClCONHOH                                                 3.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            3.121      CH.sub.2 CH(CH.sub.3)COOH                                           3.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             3.123                                                                                      ##STR64##                                                          3.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          3.125                                                                                      ##STR65##                                                          3.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          3.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   3.128                                                                                      ##STR66##         108-109                                          ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                         Compounds of formula Id                                                                                      (Id)                                              ##STR67##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         4.1        H                  69-71                                            4.2        NH.sub.2           oil                                              4.3        NO.sub.2                                                            4.4        Br                                                                  4.5        I                  74-77                                            4.6        CN                                                                  4.7        OCH.sub.3                                                           4.8        N(SO.sub.2 CH.sub.3).sub.2                                          4.9        NHSO.sub.2 CH.sub.3                                                 4.10       OC.sub.3 H.sub.7 (iso)                                              4.11       O-propargyl                                                         4.12       OCH(CH.sub.3)C.tbd.CH                                               4.13       OCH.sub.2 COOCH.sub.2 CH.sub.3                                      4.14       OCH.sub.2 CH.sub.2 OCH.sub.3                                        4.15       OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                               4.16       OCH.sub.2 COOCH.sub.3                                               4.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                   4.18       OCH.sub.2 COO-benzyl                                                4.19       OCH(CH.sub.3)COObenzyl (S)                                          4.20       OCH(CH.sub.3)COObenzyl (R)                                          4.21       OCH(CH.sub.3)COObenzyl (R,S)                                        4.22       SC.sub.3 H.sub.7 (iso)                                              4.23       SH                                                                  4.24       SCH.sub.2 COOCH.sub.3                                               4.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        4.26       SCH(CH.sub.3)COObenzyl (S)                                          4.27       SCH(CH.sub.3)COObenzyl (R)                                          4.28       SCH(CH.sub.3)COObenzyl (R,S)                                        4.29       SCH.sub.2 COObenzyl                                                 4.30       SO.sub.2 Cl                                                         4.31       SO.sub.2 CH.sub.3                                                   4.32       SO.sub.2 NHCH.sub.3                                                 4.33       COOH               150-151                                          4.34       COOCH.sub.3        60-61                                            4.35       COOC.sub.3 H.sub.7 (iso)                                                                          oil                                              4.36       COOC(CH.sub.3).sub.2 COOH                                                                         184-188                                          4.37       COOC(CH.sub.3).sub.2 COO-allyl                                      4.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    4.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     52-55                                            4.40       COOC(CH.sub.3).sub.2 CONH-allyl                                     4.41       CH.sub.2 CHClCOOethyl                                               4.42       CH.sub.2 CH═CH.sub.2                                            4.43       CH.sub.2 CH.sub.2 CH.sub.3                                          4.44       CH.sub.2 CH.sub.2 CF.sub.3                                          4.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 4.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 4.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               4.48       CH.sub.2 CHClCOOH                                                   4.49       CH.sub.2 CHClCOOCH.sub.3                                            4.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               4.51       CH.sub.2 CHClCONHallyl                                              4.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          4.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                   4.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                         4.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        4.56       CH.sub.2 CH.sub.2 COOH                                              4.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                       4.58       CH.sub.2 CH.sub.2 COOEt                                             4.59       CHClCHClCOOH                                                        4.60       CHClCHClCOOCH.sub.3                                                 4.61       CHClCHClCOOEt                                                       4.62       CH.sub.2 CH(OCH.sub.3)COOH                                          4.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   4.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         4.65       CH.sub.2 CH(SCH.sub.3)COOH                                          4.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   4.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         4.68       CH═CHCOOH                                                       4.69       CH═CHCOOCH.sub.3                                                4.70       CH═CHCOOEt                                                      4.71       CH═CClCOOH                                                      4.72       CH═CClCOOCH.sub.3                                               4.73       COOEt                                                               4.74       CONH.sub.2                                                          4.75                                                                                       ##STR68##                                                          4.76       CONHSO.sub.2 CH.sub.3                                               4.77       COOCH.sub.2 COOH                                                    4.78       COOCH.sub.2 COOCH.sub.3                                             4.79       COOCH(CH.sub.3)COOH                                                 4.80       COOCH(CH.sub.3)COOCH.sub.3                                          4.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        4.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 4.83       COOC(CH.sub.3).sub.2 CN                                             4.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      4.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 4.86                                                                                       ##STR69##                                                          4.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                             4.88       COOCH.sub.2 C.tbd.CH                                                4.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           4.90       COOCH(CH.sub.3)C.tbd.CH                                             4.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     4.92       NHallyl                                                             4.93       N(COCH.sub.3)allyl                                                  4.94       N(Et)SO.sub.2 CH.sub.3                                              4.95       N(allyl)SO.sub.2 CH.sub.3                                           4.96       N(allyl)SO.sub.2 Et                                                 4.97       SO.sub.2 N(CH.sub.3).sub.2                                          4.98       SO.sub.2 NH.sub.2                                                   4.99       SO.sub.2 NHCOCH.sub.3                                               4.100      OH                                                                  4.101      OEt                                                                 4.102      Oallyl                                                              4.103      OCH.sub.2 C.tbd.CCH.sub.3                                           4.104      OCH(CH.sub.3)CH═CH.sub.2                                        4.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               4.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     4.107                                                                                      ##STR70##                                                          4.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       4.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            4.110      OCH.sub.2 CH.sub.2 COOH                                             4.111      OC(CH.sub.3).sub.2 COOH                                             4.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      4.113      OC(CH.sub.3).sub.2 COOEt                                            4.114      OCH.sub.2 COOH                                                      4.115      OSO.sub.2 CH.sub.3                                                  4.116      OSO.sub.2 CF.sub.3                                                  4.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     4.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             4.119      CH.sub.2 CHClCONHOH                                                 4.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            4.121      CH.sub.2 CH(CH.sub.3)COOH                                           4.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             4.123                                                                                      ##STR71##                                                          4.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          4.125                                                                                      ##STR72##                                                          4.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          4.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   4.128                                                                                      ##STR73##                                                          ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                         Compounds of formula Ie                                                                                      (Ie)                                              ##STR74##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         5.1        H                  120-121                                          5.2        NH.sub.2           136-139                                          5.3        NO.sub.2           151-153                                          5.4        Br                                                                  5.5        I                  83-86                                            5.6        CN                                                                  5.7        OCH.sub.3                                                           5.8        N(SO.sub.2 CH.sub.3).sub.2                                          5.9        NHSO.sub.2 CH.sub.3                                                 5.10       OC.sub.3 H.sub.7 (iso)                                              5.11       O-propargyl                                                         5.12       OCH(CH.sub.3)C.tbd.CH                                               5.13       OCH.sub.2 COOCH.sub.2 CH.sub.3                                      5.14       OCH.sub.2 CH.sub.2 OCH.sub.3                                        5.15       OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                               5.16       OCH.sub.2 COOCH.sub.3                                               5.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                   5.18       OCH.sub.2 COO-benzyl                                                5.19       OCH(CH.sub.3)COObenzyl (S)                                          5.20       OCH(CH.sub.3)COObenzyl (R)                                          5.21       OCH(CH.sub.3)COObenzyl (R,S)                                        5.22       SC.sub.3 H.sub.7 (iso)                                              5.23       SH                                                                  5.24       SCH.sub.2 COOCH.sub.3                                               5.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        5.26       SCH(CH.sub.3)COObenzyl (S)                                          5.27       SCH(CH.sub.3)COObenzyl (R)                                          5.28       SCH(CH.sub.3)COObenzyl (R,S)                                        5.29       SCH.sub.2 COObenzyl                                                 5.30       SO.sub.2 Cl                                                         5.31       SO.sub.2 CH.sub.3                                                   5.32       SO.sub.2 NHCH.sub.3                                                 5.33       COOH               161-165                                          5.34       COOCH.sub.3        95-97                                            5.35       COOC.sub.3 H.sub.7 (iso)                                                                          117-120                                          5.36       COOC(CH.sub.3).sub.2 COOH                                           5.37       COOC(CH.sub.3).sub.2 COO-allyl                                      5.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    5.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     oil                                              5.40       COOC(CH.sub.3).sub.2 CONH-allyl                                     5.41       CH.sub.2 CHClCOOethyl                                               5.42       CH.sub.2 CH═CH.sub.2                                            5.43       CH.sub.2 CH.sub.2 CH.sub.3                                          5.44       CH.sub.2 CH.sub.2 CF.sub.3                                          5.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 5.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 5.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               5.48       CH.sub.2 CHClCOOH                                                   5.49       CH.sub.2 CHClCOOCH.sub.3                                            5.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               5.51       CH.sub.2 CHClCONHallyl                                              5.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          5.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                   5.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                         5.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        5.56       CH.sub.2 CH.sub.2 COOH                                              5.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                       5.58       CH.sub.2 CH.sub.2 COOEt                                             5.59       CHClCHClCOOH                                                        5.60       CHClCHClCOOCH.sub.3                                                 5.61       CHClCHClCOOEt                                                       5.62       CH.sub.2 CH(OCH.sub.3)COOH                                          5.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   5.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         5.65       CH.sub.2 CH(SCH.sub.3)COOH                                          5.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   5.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         5.68       CH═CHCOOH                                                       5.69       CH═CHCOOCH.sub.3                                                5.70       CH═CHCOOEt                                                      5.71       CH═CClCOOH                                                      5.72       CH═CClCOOCH.sub.3                                               5.73       COOEt                                                               5.74       CONH.sub.2                                                          5.75                                                                                       ##STR75##                                                          5.76       CONHSO.sub.2 CH.sub.3                                               5.77       COOCH.sub.2 COOH                                                    5.78       COOCH.sub.2 COOCH.sub.3                                             5.79       COOCH(CH.sub.3)COOH                                                 5.80       COOCH(CH.sub.3)COOCH.sub.3                                          5.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        5.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 5.83       COOC(CH.sub.3).sub.2 CN                                             5.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      5.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 5.86                                                                                       ##STR76##                                                          5.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                             5.88       COOCH.sub.2 C.tbd.CH                                                5.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           5.90       COOCH(CH.sub.3)C.tbd.CH                                             5.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     5.92       NHallyl                                                             5.93       N(COCH.sub.3)allyl                                                  5.94       N(Et)SO.sub.2 CH.sub.3                                              5.95       N(allyl)SO.sub.2 CH.sub.3                                           5.96       N(allyl)SO.sub.2 Et                                                 5.97       SO.sub.2 N(CH.sub.3).sub.2                                          5.98       SO.sub.2 NH.sub.2                                                   5.99       SO.sub.2 NHCOCH.sub.3                                               5.100      OH                                                                  5.101      OEt                                                                 5.102      Oallyl                                                              5.103      OCH.sub.2 C.tbd.CCH.sub.3                                           5.104      OCH(CH.sub.3)CH═CH.sub.2                                        5.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               5.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     5.107                                                                                      ##STR77##                                                          5.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       5.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            5.110      OCH.sub.2 CH.sub.2 COOH                                             5.111      OC(CH.sub.3).sub.2 COOH                                             5.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      5.113      OC(CH.sub.3).sub.2 COOEt                                            5.114      OCH.sub.2 COOH                                                      5.115      OSO.sub.2 CH.sub.3                                                  5.116      OSO.sub.2 CF.sub.3                                                  5.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     5.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             5.119      CH.sub.2 CHClCONHOH                                                 5.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            5.121      CH.sub.2 CH(CH.sub.3)COOH                                           5.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             5.123                                                                                      ##STR78##                                                          5.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          5.125                                                                                      ##STR79##                                                          5.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          5.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   5.128                                                                                      ##STR80##                                                          ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                         Compounds of formula If                                                                                       (If)                                             ##STR81##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         6.1        H                  122-124                                          6.2        NH.sub.2           140-144                                          6.3        NO.sub.2           175-176                                          6.4        Br                                                                  6.5        I                  155-159                                          6.6        CN                                                                  6.7        OCH.sub.3                                                           6.8        N(SO.sub.2 CH.sub.3).sub.2                                          6.9        NHSO.sub.2 CH.sub.3                                                 6.10       OC.sub.3 H.sub.7 (iso)                                              6.11       O-propargyl                                                         6.12       OCH(CH.sub.3)C.tbd.CH                                               6.13       OCH.sub.2 COOCH.sub.2 CH.sub.3                                      6.14       OCH.sub.2 CH.sub.2 OCH.sub.3                                        6.15       OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                               6.16       OCH.sub.2 COOCH.sub.3                                               6.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                   6.18       OCH.sub.2 COO-benzyl                                                6.19       OCH(CH.sub.3)COObenzyl (S)                                          6.20       OCH(CH.sub.3)COObenzyl (R)                                          6.21       OCH(CH.sub.3)COObenzyl (R,S)                                        6.22       SC.sub.3 H.sub.7 (iso)                                              6.23       SH                                                                  6.24       SCH.sub.2 COOCH.sub.3                                               6.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        6.26       SCH(CH.sub.3)COObenzyl (S)                                          6.27       SCH(CH.sub.3)COObenzyl (R)                                          6.28       SCH(CH.sub.3)COObenzyl (R,S)                                        6.29       SCH.sub.2 COObenzyl                                                 6.30       SO.sub.2 Cl                                                         6.31       SO.sub.2 CH.sub.3                                                   6.32       SO.sub.2 NHCH.sub.3                                                 6.33       COOH               225-227                                          6.34       COOCH.sub.3        104-106                                          6.35       COOC.sub.3 H.sub.7 (iso)                                                                          98-99                                            6.36       COOC(CH.sub.3).sub.2 COOH                                                                         173-177                                          6.37       COOC(CH.sub.3).sub.2 COO-allyl                                      6.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    6.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     90-92                                            6.40       COOC(CH.sub.3).sub.2 CONH-allyl                                     6.41       CH.sub.2 CHClCOOethyl                                               6.42       CH.sub.2 CH═CH.sub.2                                            6.43       CH.sub.2 CH.sub.2 CH.sub.3                                          6.44       CH.sub.2 CH.sub.2 CF.sub.3                                          6.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 6.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 6.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               6.48       CH.sub.2 CHClCOOH                                                   6.49       CH.sub.2 CHClCOOCH.sub.3                                            6.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               6.51       CH.sub.2 CHClCONHallyl                                              6.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          6.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                   6.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                         6.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        6.56       CH.sub.2 CH.sub.2 COOH                                              6.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                       6.58       CH.sub.2 CH.sub.2 COOEt                                             6.59       CHClCHClCOOH                                                        6.60       CHClCHClCOOCH.sub.3                                                 6.61       CHClCHClCOOEt                                                       6.62       CH.sub.2 CH(OCH.sub.3)COOH                                          6.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   6.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         6.65       CH.sub.2 CH(SCH.sub.3)COOH                                          6.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   6.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         6.68       CH═CHCOOH                                                       6.69       CH═CHCOOCH.sub.3                                                6.70       CH═CHCOOEt                                                      6.71       CH═CClCOOH                                                      6.72       CH═CClCOOCH.sub.3                                               6.73       COOEt                                                               6.74       CONH.sub.2                                                          6.75                                                                                       ##STR82##                                                          6.76       CONHSO.sub.2 CH.sub.3                                               6.77       COOCH.sub.2 COOH                                                    6.78       COOCH.sub.2 COOCH.sub.3                                             6.79       COOCH(CH.sub.3)COOH                                                 6.80       COOCH(CH.sub.3)COOCH.sub.3                                          6.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        6.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 6.83       COOC(CH.sub.3).sub.2 CN                                             6.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      6.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 6.86                                                                                       ##STR83##                                                          6.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                             6.88       COOCH.sub.2 C.tbd.CH                                                6.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           6.90       COOCH(CH.sub.3)C.tbd.CH                                             6.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     6.92       NHallyl                                                             6.93       N(COCH.sub.3)allyl                                                  6.94       N(Et)SO.sub.2 CH.sub.3                                              6.95       N(allyl)SO.sub.2 CH.sub.3                                           6.96       N(allyl)SO.sub.2 Et                                                 6.97       SO.sub.2 N(CH.sub.3).sub.2                                          6.98       SO.sub.2 NH.sub.2                                                   6.99       SO.sub.2 NHCOCH.sub.3                                               6.100      OH                                                                  6.101      OEt                                                                 6.102      Oallyl                                                              6.103      OCH.sub.2 C.tbd.CCH.sub.3                                           6.104      OCH(CH.sub.3)CH═CH.sub.2                                        6.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               6.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     6.107                                                                                      ##STR84##                                                          6.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       6.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            6.110      OCH.sub.2 CH.sub.2 COOH                                             6.111      OC(CH.sub.3).sub.2 COOH                                             6.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      6.113      OC(CH.sub.3).sub.2 COOEt                                            6.114      OCH.sub.2 COOH                                                      6.115      OSO.sub.2 CH.sub.3                                                  6.116      OSO.sub.2 CF.sub.3                                                  6.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     6.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             6.119      CH.sub.2 CHClCONHOH                                                 6.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            6.121      CH.sub.2 CH(CH.sub.3)COOH                                           6.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             6.123                                                                                      ##STR85##                                                          6.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          6.125                                                                                      ##STR86##                                                          6.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          6.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   6.128                                                                                      ##STR87##                                                          ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                         Compounds of formula Ig                                                                                      (Ig)                                              ##STR88##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         7.1        H                  oil                                              7.2        NO.sub.2                                                            7.3        Br                                                                  7.4        I                  88-90                                            7.5        CN                                                                  7.6        OCH.sub.3          88-90                                            7.7        N(SO.sub.2 CH.sub.3).sub.2                                                                        196-198                                          7.8        NHSO.sub.2 CH.sub.3                                                                               120-122                                          7.9        OC.sub.3 H.sub.7 (iso)                                              7.10       O-propargyl        88-89                                            7.11       OCH(CH.sub.3)C.tbd.CH                                               7.12       O-phenyl                                                            7.13       O-2-pyridyl                                                         7.14       O-2-pyrimidinyl                                                     7.15       OCH.sub.2 COOC.sub.2 H.sub.5                                                                      115-116                                          7.16       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                                                 74-76                                            7.17       OCH.sub.2 COO-benzyl                                                7.18       OCH(CH.sub.3)COObenzyl (S)                                          7.19       OCH(CH.sub.3)COObenzyl (R)                                          7.20       OCH(CH.sub.3)COObenzyl (R,S)                                        7.21       SC.sub.3 H.sub.7 (iso)                                                                            oil                                              7.22       SH                 78-80                                            7.23       SCH.sub.2 COOCH.sub.3                                               7.24       SCH.sub.2 COOC.sub.2 H.sub.5                                                                      106-108                                          7.25       SCH(CH.sub.3)COObenzyl (S)                                          7.26       SCH(CH.sub.3)COObenzyl (R)                                          7.27       SCH(CH.sub.3)COObenzyl (R,S)                                        7.28       SCH.sub.2 COObenzyl                                                 7.29       SO.sub.2 Cl        121-123                                          7.30       SO.sub.2 CH.sub.3                                                   7.31       SO.sub.2 NHCH.sub.3                                                                               152-153                                          7.32       COOH               210-217                                          7.33       COOCH.sub.3        92-93                                            7.34       COOC.sub.3 H.sub.7 (iso)                                                                          oil                                              7.35       COOC(CH.sub.3).sub.2 COOH                                                                         157-162                                          7.36       COOC(CH.sub.3).sub.2 COO-allyl                                      7.37       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    7.38       COOC(CH.sub.3).sub.2 COOethyl                                                                     79.5-81.5                                        7.39       COOC(CH.sub.3).sub.2 CONH-allyl                                                                   resin                                            7.40       CH.sub.2 CHClCOOethyl                                                                             oil                                              7.41       CH.sub.2 CH═CH.sub.2                                                                          oil                                              7.42       CH.sub.2 CH.sub.2 CH.sub.3                                                                        oil                                              7.43       CH.sub.2 CH.sub.2 CF.sub.3                                                                        74-76                                            7.44       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 7.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 7.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               7.47       CH.sub.2 CHClCOOH  98-99                                            7.48       CH.sub.2 CHClCOOCH.sub.3                                                                          oil                                              7.49       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               7.50       CH.sub.2 CHClCONHallyl                                              7.51       CH.sub.2 C(CH.sub.3)ClCOOH                                          7.52       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                                                 oil                                              7.53       CH.sub.2 C(CH.sub.3)ClCOOEt                                         7.54       CH.sub.2 C(CH.sub.3)ClCONHEt                                        7.55       CH.sub.2 CH.sub.2 COOH                                              7.56       CH.sub.2 CH.sub.2 COOCH.sub.3                                                                     110-111                                          7.57       CH.sub.2 CH.sub.2 COOEt                                             7.58       CHClCHClCOOH                                                        7.59       CHClCHClCOOCH.sub.3                                                 7.60       CHClCHClCOOEt                                                       7.61       CH.sub.2 CH(OCH.sub.3)COOH                                          7.62       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   7.63       CH.sub.2 CH(OCH.sub.3)COOEt                                         7.64       CH.sub.2 CH(SCH.sub.3)COOH                                          7.65       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   7.66       CH.sub.2 CH(SCH.sub.3)COOEt                                         7.67       CH═CHCOOH                                                       7.68       CH═CHCOOCH.sub.3                                                                              148-149                                          7.69       CH═CHCOOEt                                                      7.70       CH═CClCOOH                                                      7.71       CH═CClCOOCH.sub.3                                               7.72       COOEt                                                               7.73       CONH.sub.2                                                          7.74                                                                                       ##STR89##                                                          7.75       CONHSO.sub.2 CH.sub.3                                               7.76       COOCH.sub.2 COOH                                                    7.77       COOCH.sub.2 COOCH.sub.3                                             7.78       COOCH(CH.sub.3)COOH                                                 7.79       COOCH(CH.sub.3)COOCH.sub.3                                          7.80       COOCH(CH.sub.3)CH.sub.2 COOH                                        7.81       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 7.82       COOC(CH.sub.3).sub.2 CN                                             7.83       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      7.84       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 7.85                                                                                       ##STR90##                                                          7.86       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                                                           oil                                              7.87       COOCH.sub.2 C.tbd.CH                                                7.88       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           7.89       COOCH(CH.sub.3)C.tbd.CH                                             7.90       COOC(CH.sub.3).sub.2 COCH.sub.3                                     7.91       NHallyl                                                             7.92       N(COCH.sub.3)allyl                                                  7.93       N(Et)SO.sub.2 CH.sub.3                                              7.94       N(allyl)SO.sub.2 CH.sub.3                                           7.95       N(allyl)SO.sub.2 Et                                                 7.96       SO.sub.2 N(CH.sub.3).sub.2                                                                        oil                                              7.97       SO.sub.2 NH.sub.2  181-182                                          7.98       SO.sub.2 NHCOCH.sub.3                                               7.99       OH                 164-166                                          7.100      OEt                                                                 7.101      Oallyl                                                              7.102      OCH.sub.2 C.tbd.CCH.sub.3                                           7.103      OCH(CH.sub.3)CH═CH.sub.2                                        7.104      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               7.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     7.106                                                                                      ##STR91##                                                          7.107      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       7.108      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            7.109      OCH.sub.2 CH.sub.2 COOH                                             7.110      OC(CH.sub.3).sub.2 COOH                                             7.111      OC(CH.sub.3).sub.2 COOCH.sub.3                                      7.112      OC(CH.sub.3).sub.2 COOEt                                            7.113      OCH.sub.2 COOH                                                      7.114      OSO.sub.2 CH.sub.3                                                  7.115      OSO.sub.2 CF.sub.3                                                  7.116      Cl                 58-60                                            7.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     7.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             7.119      CH.sub.2 CHClCONHOH                                                 7.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            7.121      CH.sub.2 CH(CH.sub.3)COOH                                           7.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             7.123                                                                                      ##STR92##                                                          7.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          7.125                                                                                      ##STR93##                                                          7.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          7.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   7.128                                                                                      ##STR94##                                                          7.129      CH═CH--CF.sub.3                                                                               102--103                                         ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                         Compounds of formula Ih                                                                                      (Ih)                                              ##STR95##                                                                     Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         8.1        H                   98-100                                          8.2        NH.sub.2           164-165                                          8.3        NO.sub.2           164-165                                          8.4        Br                                                                  8.5        I                                                                   8.6        CN                                                                  8.7        OCH.sub.3          152-153                                          8.8        N(SO.sub.2 CH.sub.3).sub.2                                                                        246-248                                          8.9        NHSO.sub.2 CH.sub.3                                                                               153-154                                          8.10       OC.sub.3 H.sub.7 (iso)                                              8.11       O-propargyl        151-152                                          8.12       OCH(CH.sub.3)C.tbd.CH                                               8.13       O-phenyl                                                            8.14       O-2-pyridyl                                                         8.15       O-2-pyrimidinyl                                                     8.16       OCH.sub.2 COOC.sub.2 H.sub.5                                                                      165-166                                          8.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                                                 89-91                                            8.18       OCH.sub.2 COO-benzyl                                                8.19       OCH(CH.sub.3)COObenzyl (S)                                          8.20       OCH(CH.sub.3)COObenzyl (R)                                          8.21       OCH(CH.sub.3)COObenzyl (R,S)                                        8.22       SC.sub.3 H.sub.7 (iso)                                              8.23       SH                                                                  8.24       SCH.sub.2 COOCH.sub.3                                               8.25       SCH.sub.2 COOC.sub.2 H.sub.5                                        8.26       SCH(CH.sub.3)COObenzyl (S)                                          8.27       SCH(CH.sub.3)COObenzyl (R)                                          8.28       SCH(CH.sub.3)COObenzyl (R,S)                                        8.29       SCH.sub.2 COObenzyl                                                 8.30       SO.sub.2 Cl        160-163                                          8.31       SO.sub.2 CH.sub.3                                                   8.32       SO.sub.2 NHCH.sub.3                                                 8.33       COOH               78-86                                            8.34       COOCH.sub.3        134-136                                          8.35       COOC.sub.3 H.sub.7 (iso)                                                                          116-119                                          8.36       COOC(CH.sub.3).sub.2 COOH                                                                         78-86                                            8.37       COOC(CH.sub.3).sub.2 COO-allyl                                      8.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    8.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     oil                                              8.40       COOC(CH.sub.3).sub.2 CONH-allyl                                                                   168-172                                          8.41       CH.sub.2 CHClCOOethyl                                                                             87-89                                            8.42       CH.sub.2 CH═CH.sub.2                                                                          118-120                                          8.43       CH.sub.2 CH.sub.2 CH.sub.3                                                                        128-129                                          8.44       CH.sub.2 CH.sub.2 CF.sub.3                                          8.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 8.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 8.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               8.48       CH.sub.2 CHClCOOH  92-94                                            8.49       CH.sub.2 CHClCOOCH.sub.3                                                                          95-96                                            8.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               8.51       CH.sub.2 CHClCONHallyl                                              8.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          8.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                                                 oil                                              8.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                         8.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        8.56       CH.sub.2 CH.sub.2 COOH                                              8.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                                                     153-154                                          8.58       CH.sub.2 CH.sub.2 COOEt                                             8.59       CHClCHClCOOH                                                        8.60       CHClCHClCOOCH.sub.3                                                 8.61       CHClCHClCOOEt                                                       8.62       CH.sub.2 CH(OCH.sub.3)COOH                                          8.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   8.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         8.65       CH.sub.2 CH(SCH.sub.3)COOH                                          8.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   8.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         8.68       CH═CHCOOH                                                       8.69       CH═CHCOOCH.sub.3                                                8.70       CH═CHCOOEt                                                      8.71       CH═CClCOOH                                                      8.72       CH═CClCOOCH.sub.3                                               8.73       COOEt              122-123                                          8.74       CONH.sub.2                                                          8.75                                                                                       ##STR96##                                                          8.76       CONHSO.sub.2 CH.sub.3                                               8.77       COOCH.sub.2 COOH                                                    8.78       COOCH.sub.2 COOCH.sub.3                                             8.79       COOCH(CH.sub.3)COOH                                                 8.80       COOCH(CH.sub.3)COOCH.sub.3                                          8.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        8.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 8.83       COOC(CH.sub.3).sub.2 CN                                             8.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      8.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 8.86                                                                                       ##STR97##                                                          8.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                                                           oil                                              8.88       COOCH.sub.2 C.tbd.CH                                                8.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           8.90       COOCH(CH.sub.3)C.tbd.CH                                             8.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     8.92       NHallyl                                                             8.93       N(COCH.sub.3)allyl                                                  8.94       N(Et)SO.sub.2 CH.sub.3                                              8.95       N(allyl)SO.sub.2 CH.sub.3                                           8.96       N(allyl)SO.sub.2 Et                                                 8.97       SO.sub.2 N(CH.sub.3).sub.2                                          8.98       SO.sub.2 NH.sub.2                                                   8.99       SO.sub.2 NHCOCH.sub.3                                               8.100      OH                                                                  8.101      OEt                                                                 8.102      Oallyl                                                              8.103      OCH.sub.2 C.tbd.CCH.sub.3                                           8.104      OCH(CH.sub.3)CH═CH.sub.2                                        8.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               8.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     8.107                                                                                      ##STR98##                                                          8.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       8.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            8.110      OCH.sub.2 CH.sub.2 COOH                                             8.111      OC(CH.sub.3).sub.2 COOH                                             8.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      8.113      OC(CH.sub.3).sub.2 COOEt                                            8.114      OCH.sub.2 COOH                                                      8.115      OSO.sub.2 CH.sub.3                                                  8.116      OSO.sub.2 CF.sub.3                                                  8.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     8.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             8.119      CH.sub.2 CHClCONHOH                                                 8.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            8.121      CH.sub.2 CH(CH.sub.3)COOH                                           8.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             8.123                                                                                      ##STR99##                                                          8.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          8.125                                                                                      ##STR100##                                                         8.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          8.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   8.128                                                                                      ##STR101##                                                         8.129      CH═CH--CF.sub.3                                                 ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         Compounds of formula Ii                                                                                      (Ii)                                              ##STR102##                                                                    Comp. No.  R.sub.6            M.p.                                             ______________________________________                                         9.1        H                  110-112                                          9.2        NH.sub.2           185-187                                          9.3        NO.sub.2           156-159                                          9.4        Br                                                                  9.5        I                  167-170                                          9.6        CN                                                                  9.7        OCH.sub.3          150-151                                          9.8        N(SO.sub.2 CH.sub.3).sub.2                                                                        265-267                                          9.9        NHSO.sub.2 CH.sub.3                                                                               185-187                                          9.10       OC.sub.3 H.sub.7 (iso)                                              9.11       O-propargyl        126-127                                          9.12       OCH(CH.sub.3)C.tbd.CH                                               9.13       O-phenyl                                                            9.14       O-2-pyridyl                                                         9.15       O-2-pyrimidinyl                                                     9.16       OCH.sub.2 COOC.sub.2 H.sub.5                                                                      140-141                                          9.17       OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                                                 118-120                                          9.18       OCH.sub.2 COO-benzyl                                                9.19       OCH(CH.sub.3)COObenzyl (S)                                          9.20       OCH(CH.sub.3)COObenzyl (R)                                          9.21       OCH(CH.sub.3)COObenzyl (R,S)                                        9.22       SC.sub.3 H.sub.7 (iso)                                                                            93-95                                            9.23       SH                                                                  9.24       SCH.sub.2 COOCH.sub.3                                               9.25       SCH.sub.2 COOC.sub.2 H.sub.5                                                                      133-135                                          9.26       SCH(CH.sub.3)COObenzyl (S)                                          9.27       SCH(CH.sub.3)COObenzyl (R)                                          9.28       SCH(CH.sub.3)COObenzyl (R,S)                                        9.29       SCH.sub.2 COObenzyl                                                 9.30       SO.sub.2 Cl        169-171                                          9.31       SO.sub.2 CH.sub.3                                                   9.32       SO.sub.2 NHCH.sub.3                                                 9.33       COOH               201-208                                          9.34       COOCH.sub.3        137-139                                          9.35       COOC.sub.3 H.sub.7 (iso)                                                                          111-114                                          9.36       COOC(CH.sub.3).sub.2 COOH                                                                         179-182                                          9.37       COOC(CH.sub.3).sub.2 COO-allyl                                      9.38       COOC(CH.sub.3).sub.2 COOCH.sub.3                                    9.39       COOC(CH.sub.3).sub.2 COOethyl                                                                     oil                                              9.40       COOC(CH.sub.3).sub.2 CONH-allyl                                                                   141-143                                          9.41       CH.sub.2 CHClCOOethyl                                                                             oil                                              9.42       CH.sub.2 CH═CH.sub.2                                                                          oil                                              9.43       CH.sub.2 CH.sub.2 CH.sub.3                                                                        107-109                                          9.44       CH.sub.2 CH.sub.2 CF.sub.3                                          9.45       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                 9.46       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                 9.47       OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                               9.48       CH.sub.2 CHClCOOH  185-187                                          9.49       CH.sub.2 CHClCOOCH.sub.3                                                                          96-98                                            9.50       CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                               9.51       CH.sub.2 CHClCONHallyl                                              9.52       CH.sub.2 C(CH.sub.3)ClCOOH                                          9.53       CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                                                 oil                                              9.54       CH.sub.2 C(CH.sub.3)ClCOOEt                                         9.55       CH.sub.2 C(CH.sub.3)ClCONHEt                                        9.56       CH.sub.2 CH.sub.2 COOH                                              9.57       CH.sub.2 CH.sub.2 COOCH.sub.3                                                                     152-153                                          9.58       CH.sub.2 CH.sub.2 COOEt                                             9.59       CHClCHClCOOH                                                        9.60       CHClCHClCOOCH.sub.3                                                 9.61       CHClCHClCOOEt                                                       9.62       CH.sub.2 CH(OCH.sub.3)COOH                                          9.63       CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                   9.64       CH.sub.2 CH(OCH.sub.3)COOEt                                         9.65       CH.sub.2 CH(SCH.sub.3)COOH                                          9.66       CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                   9.67       CH.sub.2 CH(SCH.sub.3)COOEt                                         9.68       CH═CHCOOH                                                       9.69       CH═CHCOOCH.sub.3                                                9.70       CH═CHCOOEt                                                      9.71       CH═CClCOOH                                                      9.72       CH═CClCOOCH.sub.3                                               9.73       COOEt              105-107                                          9.74       CONH.sub.2                                                          9.75                                                                                       ##STR103##                                                         9.76       CONHSO.sub.2 CH.sub.3                                               9.77       COOCH.sub.2 COOH                                                    9.78       COOCH.sub.2 COOCH.sub.3                                             9.79       COOCH(CH.sub.3)COOH                                                 9.80       COOCH(CH.sub.3)COOCH.sub.3                                          9.81       COOCH(CH.sub.3)CH.sub.2 COOH                                        9.82       COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                 9.83       COOC(CH.sub.3).sub.2 CN                                             9.84       COOCH.sub.2 CH.sub.2 OCH.sub.3                                      9.85       COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                 9.86                                                                                       ##STR104##                                                         9.87       COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                             9.88       COOCH.sub.2 C.tbd.CH                                                9.89       COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                           9.90       COOCH(CH.sub.3)C.tbd.CH                                             9.91       COOC(CH.sub.3).sub.2 COCH.sub.3                                     9.92       NHallyl                                                             9.93       N(COCH.sub.3)allyl                                                  9.94       N(Et)SO.sub.2 CH.sub.3                                              9.95       N(allyl)SO.sub.2 CH.sub.3                                           9.96       N(allyl)SO.sub.2 Et                                                 9.97       SO.sub.2 N(CH.sub.3).sub.2                                          9.98       SO.sub.2 NH.sub.2                                                   9.99       SO.sub.2 NHCOCH.sub.3                                               9.100      OH                 164-165                                          9.101      OEt                                                                 9.102      Oallyl                                                              9.103      OCH.sub.2 C.tbd.CCH.sub.3                                           9.104      OCH(CH.sub.3)CH═CH.sub.2                                        9.105      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                               9.106      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                     9.107                                                                                      ##STR105##                                                         9.108      OCH.sub.2 CH.sub.2 NHCH.sub.3                                       9.109      OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                            9.110      OCH.sub.2 CH.sub.2 COOH                                             9.111      OC(CH.sub.3).sub.2 COOH                                             9.112      OC(CH.sub.3).sub.2 COOCH.sub.3                                      9.113      OC(CH.sub.3).sub.2 COOEt                                            9.114      OCH.sub.2 COOH                                                      9.115      OSO.sub.2 CH.sub.3                                                  9.116      OSO.sub.2 CF.sub.3                                                  9.117      CH.sub.2 CHClCOOC.sub.2 H.sub.5                                     9.118      CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                             9.119      CH.sub.2 CHClCONHOH                                                 9.120      CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                            9.121      CH.sub.2 CH(CH.sub.3)COOH                                           9.122      CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                             9.123                                                                                      ##STR106##                                                         9.124      COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5          9.125                                                                                      ##STR107##                                                         9.126      COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                          9.127      COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                   9.128                                                                                      ##STR108##                                                         ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         Compounds of formula lj                                                                                       (lj)                                             ##STR109##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         10.1     H                      72-74                                          10.2     CN                                                                    10.3     OCH.sub.3                                                             10.4     NHSO.sub.2 CH.sub.3                                                   10.5     OC.sub.3 H.sub.7 (iso)                                                10.6     O-propargyl                                                           10.7     OCH(CH.sub.3)C.tbd.CH                                                 10.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        10.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          10.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 10.11    OCH.sub.2 COOCH.sub.3                                                 10.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     10.13    OCH.sub.2 COO-benzyl                                                  10.14    OCH(CH.sub.3)COObenzyl                                                10.15    SC.sub.3 H.sub.7 (iso)                                                10.16    SCH.sub.2 COOCH.sub.3                                                 10.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          10.18    SCH(CH.sub.3)COObenzyl                                                10.19    SCH.sub.2 COObenzyl                                                   10.20    COOCH.sub.3                                                           10.21    COOC.sub.3 H.sub.7 (iso)                                              10.22    COOC(CH.sub.3).sub.2 COOH                                             10.23    COOC(CH.sub.3).sub.2 COO-allyl                                        10.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      10.25    COOC(CH.sub.3).sub.2 COOethyl                                         10.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       10.27    CH.sub.2 CHClCOOethyl                                                 10.28    CH.sub.2 CH═CH.sub.2                                              10.29    CH.sub.2 CH.sub.2 CH.sub.3                                            10.30    CH.sub.2 CH.sub.2 CF.sub.3                                            10.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   10.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   10.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 10.34    CH.sub.2 CHClCOOH                                                     10.35    CH.sub.2 CHClCOOCH.sub.3                                              10.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 10.37    CH.sub.2 CHClCONHallyl                                                10.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            10.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     10.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           10.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          10.42    CH.sub.2 CH.sub.2 COOH                                                10.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         10.44    CH.sub.2 CH.sub.2 COOEt                                               10.45    CHClCHClCOOH                                                          10.46    CHClCHClCOOCH.sub.3                                                   10.47    CHClCHClCOOEt                                                         10.48    CH.sub.2 CH(OCH.sub.3)COOH                                            10.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     10.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           10.51    CH.sub.2 CH(SCH.sub.3)COOH                                            10.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     10.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           10.54    CH═CHCOOH                                                         10.55    CH═CHCOOCH.sub.3                                                  10.56    CH═CHCOOEt                                                        10.57    CH═CClCOOH                                                        10.58    CH═CClCOOCH.sub.3                                                 10.59    COOEt                                                                 10.60    CONH.sub.2                                                            10.61                                                                                    ##STR110##                                                           10.62    CONHSO.sub.2 CH.sub.3                                                 10.63    COOCH.sub.2 COOH                                                      10.64    COOCH.sub.2 COOCH.sub.3                                               10.65    COOCH(CH.sub.3)COOH                                                   10.66    COOCH(CH.sub.3)COOCH.sub.3                                            10.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          10.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   10.69    COOC(CH.sub.3).sub.2 CN                                               10.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        10.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   10.72                                                                                    ##STR111##                                                           10.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               10.74    COOCH.sub.2 C.tbd.CH                                                  10.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             10.76    COOCH(CH.sub.3)C.tbd.CH                                               10.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       10.78    NHallyl                                                               10.79    N(COCH.sub.3)allyl                                                    10.80    N(Et)SO.sub.2 CH.sub.3                                                10.81    N(allyl)SO.sub.2 CH.sub.3                                             10.82    N(allyl)SO.sub.2 Et                                                   10.83    SO.sub.2 N(CH.sub.3).sub.2                                            10.84    SO.sub.2 NH.sub.2                                                     10.85    SO.sub.2 NHCOCH.sub.3                                                 10.86    OH                                                                    10.87    OEt                                                                   10.88    Oallyl                                                                10.89    OCH.sub.2 C.tbd.CCH.sub.3                                             10.90    OCH(CH.sub.3)CH═CH.sub.2                                          10.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 10.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       10.93                                                                                    ##STR112##                                                           10.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         10.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              10.96    OCH.sub.2 CH.sub.2 COOH                                               10.97    OC(CH.sub.3).sub.2 COOH                                               10.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        10.99    OC(CH.sub.3).sub.2 COOEt                                              10.100   OCH.sub.2 COOH                                                        10.101   OSO.sub.2 CH.sub.3                                                    10.102   OSO.sub.2 CF.sub.3                                                    10.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       10.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               10.105   CH.sub.2 CHClCONHOH                                                   10.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              10.107   CH.sub.2 CH(CH.sub.3)COOH                                             10.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               10.109                                                                                   ##STR113##                                                           10.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            10.111                                                                                   ##STR114##                                                           10.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            10.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     10.114                                                                                   ##STR115##                                                           ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                         Compounds of formula lk                                                                                      (lk)                                              ##STR116##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         11.1     H                      88-91                                          11.2     CN                                                                    11.3     OCH.sub.3                                                             11.4     NHSO.sub.2 CH.sub.3                                                   11.5     OC.sub.3 H.sub.7 (iso)                                                11.6     O-propargyl                                                           11.7     OCH(CH.sub.3)C.tbd.CH                                                 11.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        11.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          11.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 11.11    OCH.sub.2 COOCH.sub.3                                                 11.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     11.13    OCH.sub.2 COO-benzyl                                                  11.14    OCH(CH.sub.3)COObenzyl                                                11.15    SC.sub.3 H.sub.7 (iso)                                                11.16    SCH.sub.2 COOCH.sub.3                                                 11.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          11.18    SCH(CH.sub.3)COObenzyl                                                11.19    SCH.sub.2 COObenzyl                                                   11.20    COOCH.sub.3                                                           11.21    COOC.sub.3 H.sub.7 (iso)                                              11.22    COOC(CH.sub.3).sub.2 COOH                                             11.23    COOC(CH.sub.3).sub.2 COO-allyl                                        11.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      11.25    COOC(CH.sub.3).sub.2 COOethyl                                         11.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       11.27    CH.sub.2 CHClCOOethyl                                                 11.28    CH.sub.2 CH═CH.sub.2                                              11.29    CH.sub.2 CH.sub.2 CH.sub.3                                            11.30    CH.sub.2 CH.sub.2 CF.sub.3                                            11.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   11.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   11.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 11.34    CH.sub.2 CHClCOOH                                                     11.35    CH.sub.2 CHClCOOCH.sub.3                                              11.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 11.37    CH.sub.2 CHClCONHallyl                                                11.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            11.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     11.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           11.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          11.42    CH.sub.2 CH.sub.2 COOH                                                11.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         11.44    CH.sub.2 CH.sub.2 COOEt                                               11.45    CHClCHClCOOH                                                          11.46    CHClCHClCOOCH.sub.3                                                   11.47    CHClCHClCOOEt                                                         11.48    CH.sub.2 CH(OCH.sub.3)COOH                                            11.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     11.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           11.51    CH.sub.2 CH(SCH.sub.3)COOH                                            11.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     11.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           11.54    CH═CHCOOH                                                         11.55    CH═CHCOOCH.sub.3                                                  11.56    CH═CHCOOEt                                                        11.57    CH═CClCOOH                                                        11.58    CH═CClCOOCH.sub.3                                                 11.59    COOEt                                                                 11.60    CONH.sub.2                                                            11.61                                                                                    ##STR117##                                                           11.62    CONHSO.sub.2 CH.sub.3                                                 11.63    COOCH.sub.2 COOH                                                      11.64    COOCH.sub.2 COOCH.sub.3                                               11.65    COOCH(CH.sub.3)COOH                                                   11.66    COOCH(CH.sub.3)COOCH.sub.3                                            11.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          11.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   11.69    COOC(CH.sub.3).sub.2 CN                                               11.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        11.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   11.72                                                                                    ##STR118##                                                           11.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               11.74    COOCH.sub.2 C.tbd.CH                                                  11.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             11.76    COOCH(CH.sub.3)C.tbd.CH                                               11.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       11.78    NHallyl                                                               11.79    N(COCH.sub.3)allyl                                                    11.80    N(Et)SO.sub.2 CH.sub.3                                                11.81    N(allyl)SO.sub.2 CH.sub.3                                             11.82    N(allyl)SO.sub.2 Et                                                   11.83    SO.sub.2 N(CH.sub.3).sub.2                                            11.84    SO.sub.2 NH.sub.2                                                     11.85    SO.sub.2 NHCOCH.sub.3                                                 11.86    OH                                                                    11.87    OEt                                                                   11.88    Oallyl                                                                11.89    OCH.sub.2 C.tbd.CCH.sub.3                                             11.90    OCH(CH.sub.3)CH═CH.sub.2                                          11.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 11.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       11.93                                                                                    ##STR119##                                                           11.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         11.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              11.96    OCH.sub.2 CH.sub.2 COOH                                               11.97    OC(CH.sub.3).sub.2 COOH                                               11.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        11.99    OC(CH.sub.3).sub.2 COOEt                                              11.100   OCH.sub.2 COOH                                                        11.101   OSO.sub.2 CH.sub.3                                                    11.102   OSO.sub.2 CF.sub.3                                                    11.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       11.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               11.105   CH.sub.2 CHClCONHOH                                                   11.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              11.107   CH.sub.2 CH(CH.sub.3)COOH                                             11.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               11.109                                                                                   ##STR120##                                                           11.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            11.111                                                                                   ##STR121##                                                           11.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            11.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     11.114                                                                                   ##STR122##                                                           ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                         Compounds of formula lm                                                                                      (lm)                                              ##STR123##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         12.1     H                      91-92                                          12.2     CN                                                                    12.3     OCH.sub.3                                                             12.4     NHSO.sub.2 CH.sub.3                                                   12.5     OC.sub.3 H.sub.7 (iso)                                                12.6     O-propargyl                                                           12.7     OCH(CH.sub.3)C.tbd.CH                                                 12.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        12.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          12.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 12.11    OCH.sub.2 COOCH.sub.3                                                 12.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     12.13    OCH.sub.2 COO-benzyl                                                  12.14    OCH(CH.sub.3)COObenzyl                                                12.15    SC.sub.3 H.sub.7 (iso)                                                12.16    SCH.sub.2 COOCH.sub.3                                                 12.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          12.18    SCH(CH.sub.3)COObenzyl                                                12.19    SCH.sub.2 COObenzyl                                                   12.20    COOCH.sub.3                                                           12.21    COOC.sub.3 H.sub.7 (iso)                                              12.22    COOC(CH.sub.3).sub.2 COOH                                             12.23    COOC(CH.sub.3).sub.2 COO-allyl                                        12.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      12.25    COOC(CH.sub.3).sub.2 COOethyl                                         12.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       12.27    CH.sub.2 CHClCOOethyl                                                 12.28    CH.sub.2 CH═CH.sub.2                                              12.29    CH.sub.2 CH.sub.2 CH.sub.3                                            12.30    CH.sub.2 CH.sub.2 CF.sub.3                                            12.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   12.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   12.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 12.34    CH.sub.2 CHClCOOH                                                     12.35    CH.sub.2 CHClCOOCH.sub.3                                              12.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 12.37    CH.sub.2 CHClCONHallyl                                                12.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            12.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     12.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           12.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          12.42    CH.sub.2 CH.sub.2 COOH                                                12.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         12.44    CH.sub.2 CH.sub.2 COOEt                                               12.45    CHClCHClCOOH                                                          12.46    CHClCHClCOOCH.sub.3                                                   12.47    CHClCHClCOOEt                                                         12.48    CH.sub.2 CH(OCH.sub.3)COOH                                            12.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     12.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           12.51    CH.sub.2 CH(SCH.sub.3)COOH                                            12.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     12.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           12.54    CH═CHCOOH                                                         12.55    CH═CHCOOCH.sub.3                                                  12.56    CH═CHCOOEt                                                        12.57    CH═CClCOOH                                                        12.58    CH═CClCOOCH.sub.3                                                 12.59    COOEt                                                                 12.60    CONH.sub.2                                                            12.61                                                                                    ##STR124##                                                           12.62    CONHSO.sub.2 CH.sub.3                                                 12.63    COOCH.sub.2 COOH                                                      12.64    COOCH.sub.2 COOCH.sub.3                                               12.65    COOCH(CH.sub.3)COOH                                                   12.66    COOCH(CH.sub.3)COOCH.sub.3                                            12.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          12.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   12.69    COOC(CH.sub.3).sub.2 CN                                               12.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        12.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   12.72                                                                                    ##STR125##                                                           12.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               12.74    COOCH.sub.2 C.tbd.CH                                                  12.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             12.76    COOCH(CH.sub.3)C.tbd.CH                                               12.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       12.78    NHallyl                                                               12.79    N(COCH.sub.3)allyl                                                    12.80    N(Et)SO.sub.2 CH.sub.3                                                12.81    N(allyl)SO.sub.2 CH.sub.3                                             12.82    N(allyl)SO.sub.2 Et                                                   12.83    SO.sub.2 N(CH.sub.3).sub.2                                            12.84    SO.sub.2 NH.sub.2                                                     12.85    SO.sub.2 NHCOCH.sub.3                                                 12.86    OH                                                                    12.87    OEt                                                                   12.88    Oallyl                                                                12.89    OCH.sub.2 C.tbd.CCH.sub.3                                             12.90    OCH(CH.sub.3)CH═CH.sub.2                                          12.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 12.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       12.93                                                                                    ##STR126##                                                           12.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         12.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              12.96    OCH.sub.2 CH.sub.2 COOH                                               12.97    OC(CH.sub.3).sub.2 COOH                                               12.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        12.99    OC(CH.sub.3).sub.2 COOEt                                              12.100   OCH.sub.2 COOH                                                        12.101   OSO.sub.2 CH.sub.3                                                    12.102   OSO.sub.2 CF.sub.3                                                    12.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       12.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               12.105   CH.sub.2 CHClCONHOH                                                   12.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              12.107   CH.sub.2 CH(CH.sub.3)COOH                                             12.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               12.109                                                                                   ##STR127##                                                           12.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            12.111                                                                                   ##STR128##                                                           12.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            12.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     12.114                                                                                   ##STR129##                                                           ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                         Compounds of formula ln                                                                                      (ln)                                              ##STR130##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         13.1     H                      65-70                                          13.2     CN                                                                    13.3     OCH.sub.3                                                             13.4     NHSO.sub.2 CH.sub.3                                                   13.5     OC.sub.3 H.sub.7 (iso)                                                13.6     O-propargyl                                                           13.7     OCH(CH.sub.3)C.tbd.CH                                                 13.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        13.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          13.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 13.11    OCH.sub.2 COOCH.sub.3                                                 13.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     13.13    OCH.sub.2 COO-benzyl                                                  13.14    OCH(CH.sub.3)COObenzyl                                                13.15    SC.sub.3 H.sub.7 (iso)                                                13.16    SCH.sub.2 COOCH.sub.3                                                 13.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          13.18    SCH(CH.sub.3)COObenzyl                                                13.19    SCH.sub.2 COObenzyl                                                   13.20    COOCH.sub.3                                                           13.21    COOC.sub.3 H.sub.7 (iso)                                              13.22    COOC(CH.sub.3).sub.2 COOH                                             13.23    COOC(CH.sub.3).sub.2 COO-allyl                                        13.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      13.25    COOC(CH.sub.3).sub.2 COOethyl                                         13.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       13.27    CH.sub.2 CHClCOOethyl                                                 13.28    CH.sub.2 CH═CH.sub.2                                              13.29    CH.sub.2 CH.sub.2 CH.sub.3                                            13.30    CH.sub.2 CH.sub.2 CF.sub.3                                            13.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   13.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   13.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 13.34    CH.sub.2 CHClCOOH                                                     13.35    CH.sub.2 CHClCOOCH.sub.3                                              13.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 13.37    CH.sub.2 CHClCONHallyl                                                13.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            13.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     13.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           13.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          13.42    CH.sub.2 CH.sub.2 COOH                                                13.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         13.44    CH.sub.2 CH.sub.2 COOEt                                               13.45    CHClCHClCOOH                                                          13.46    CHClCHClCOOCH.sub.3                                                   13.47    CHClCHClCOOEt                                                         13.48    CH.sub.2 CH(OCH.sub.3)COOH                                            13.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     13.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           13.51    CH.sub.2 CH(SCH.sub.3)COOH                                            13.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     13.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           13.54    CH═CHCOOH                                                         13.55    CH═CHCOOCH.sub.3                                                  13.56    CH═CHCOOEt                                                        13.57    CH═CClCOOH                                                        13.58    CH═CClCOOCH.sub.3                                                 13.59    COOEt                                                                 13.60    CONH.sub.2                                                            13.61                                                                                    ##STR131##                                                           13.62    CONHSO.sub.2 CH.sub.3                                                 13.63    COOCH.sub.2 COOH                                                      13.64    COOCH.sub.2 COOCH.sub.3                                               13.65    COOCH(CH.sub.3)COOH                                                   13.66    COOCH(CH.sub.3)COOCH.sub.3                                            13.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          13.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   13.69    COOC(CH.sub.3).sub.2 CN                                               13.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        13.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   13.72                                                                                    ##STR132##                                                           13.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               13.74    COOCH.sub.2 C.tbd.CH                                                  13.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             13.76    COOCH(CH.sub.3)C.tbd.CH                                               13.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       13.78    NHallyl                                                               13.79    N(COCH.sub.3)allyl                                                    13.80    N(Et)SO.sub.2 CH.sub.3                                                13.81    N(allyl)SO.sub.2 CH.sub.3                                             13.82    N(allyl)SO.sub.2 Et                                                   13.83    SO.sub.2 N(CH.sub.3).sub.2                                            13.84    SO.sub.2 NH.sub.2                                                     13.85    SO.sub.2 NHCOCH.sub.3                                                 13.86    OH                                                                    13.87    OEt                                                                   13.88    Oallyl                                                                13.89    OCH.sub.2 C.tbd.CCH.sub.3                                             13.90    OCH(CH.sub.3)CH═CH.sub.2                                          13.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub..sub.3                            13.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       13.93                                                                                    ##STR133##                                                           13.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         13.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              13.96    OCH.sub.2 CH.sub.2 COOH                                               13.97    OC(CH.sub.3).sub.2 COOH                                               13.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        13.99    OC(CH.sub.3).sub.2 COOEt                                              13.100   OCH.sub.2 COOH                                                        13.101   OSO.sub.2 CH.sub.3                                                    13.102   OSO.sub.2 CF.sub.3                                                    13.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       13.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               13.105   CH.sub.2 CHClCONHOH                                                   13.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              13.107   CH.sub.2 CH(CH.sub.3)COOH                                             13.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               13.109                                                                                   ##STR134##                                                           13.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            13.111                                                                                   ##STR135##                                                           13.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            13.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     13.114                                                                                   ##STR136##                                                           ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                         Compounds of formula lo                                                                                      (lo)                                              ##STR137##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         14.1     H                      115-117                                        14.2     CN                                                                    14.3     OCH.sub.3                                                             14.4     NHSO.sub.2 CH.sub.3                                                   14.5     OC.sub.3 H.sub.7 (iso)                                                14.6     O-propargyl                                                           14.7     OCH(CH.sub.3)C.tbd.CH                                                 14.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        14.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          14.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 14.11    OCH.sub.2 COOCH.sub.3                                                 14.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     14.13    OCH.sub.2 COO-benzyl                                                  14.14    OCH(CH.sub.3)COObenzyl                                                14.15    SC.sub.3 H.sub.7 (iso)                                                14.16    SCH.sub.2 COOCH.sub.3                                                 14.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          14.18    SCH(CH.sub.3)COObenzyl                                                14.19    SCH.sub.2 COObenzyl                                                   14.20    COOCH.sub.3                                                           14.21    COOC.sub.3 H.sub.7 (iso)                                              14.22    COOC(CH.sub.3).sub.2 COOH                                             14.23    COOC(CH.sub.3).sub.2 COO-allyl                                        14.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      14.25    COOC(CH.sub.3).sub.2 COOethyl                                         14.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       14.27    CH.sub.2 CHClCOOethyl                                                 14.28    CH.sub.2 CH═CH.sub.2                                              14.29    CH.sub.2 CH.sub.2 CH.sub.3                                            14.30    CH.sub.2 CH.sub.2 CF.sub.3                                            14.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   14.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   14.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 14.34    CH.sub.2 CHClCOOH                                                     14.35    CH.sub.2 CHClCOOCH.sub.3                                              14.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 14.37    CH.sub.2 CHClCONHallyl                                                14.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            14.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     14.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           14.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          14.42    CH.sub.2 CH.sub.2 COOH                                                14.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         14.44    CH.sub.2 CH.sub.2 COOEt                                               14.45    CHClCHClCOOH                                                          14.46    CHClCHClCOOCH.sub.3                                                   14.47    CHClCHClCOOEt                                                         14.48    CH.sub.2 CH(OCH.sub.3)COOH                                            14.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     14.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           14.51    CH.sub.2 CH(SCH.sub.3)COOH                                            14.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     14.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           14.54    CH═CHCOOH                                                         14.55    CH═CHCOOCH.sub.3                                                  14.56    CH═CHCOOEt                                                        14.57    CH═CClCOOH                                                        14.58    CH═CClCOOCH.sub.3                                                 14.59    COOEt                                                                 14.60    CONH.sub.2                                                            14.61                                                                                    ##STR138##                                                           14.62    CONHSO.sub.2 CH.sub.3                                                 14.63    COOCH.sub.2 COOH                                                      14.64    COOCH.sub.2 COOCH.sub.3                                               14.65    COOCH(CH.sub.3)COOH                                                   14.66    COOCH(CH.sub.3)COOCH.sub.3                                            14.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          14.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   14.69    COOC(CH.sub.3).sub.2 CN                                               14.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        14.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   14.72                                                                                    ##STR139##                                                           14.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               14.74    COOCH.sub.2 C.tbd.CH                                                  14.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             14.76    COOCH(CH.sub.3)C.tbd.CH                                               14.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       14.78    NHallyl                                                               14.79    N(COCH.sub.3)allyl                                                    14.80    N(Et)SO.sub.2 CH.sub.3                                                14.81    N(allyl)SO.sub.2 CH.sub.3                                             14.82    N(allyl)SO.sub.2 Et                                                   14.83    SO.sub.2 N(CH.sub.3).sub.2                                            14.84    SO.sub.2 NH.sub.2                                                     14.85    SO.sub.2 NHCOCH.sub.3                                                 14.86    OH                                                                    14.87    OEt                                                                   14.88    Oallyl                                                                14.89    OCH.sub.2 C.tbd.CCH.sub.3                                             14.90    OCH(CH.sub.3)CH═CH.sub.2                                          14.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 14.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       14.93                                                                                    ##STR140##                                                           14.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         14.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              14.96    OCH.sub.2 CH.sub.2 COOH                                               14.97    OC(CH.sub.3).sub.2 COOH                                               14.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        14.99    OC(CH.sub.3).sub.2 COOEt                                              14.100   OCH.sub.2 COOH                                                        14.101   OSO.sub.2 CH.sub.3                                                    14.102   OSO.sub.2 CF.sub.3                                                    14.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       14.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               14.105   CH.sub.2 CHClCONHOH                                                   14.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              14.107   CH.sub.2 CH(CH.sub.3)COOH                                             14.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               14.109                                                                                   ##STR141##                                                           14.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            14.111                                                                                   ##STR142##                                                           14.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            14.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     14.114                                                                                   ##STR143##                                                           ______________________________________                                    

                  TABLE 15                                                         ______________________________________                                         Compounds of formula lp                                                                                      (lp)                                              ##STR144##                                                                    Comp. No.                                                                               R.sub.6                M.p.                                           ______________________________________                                         15.1     H                      110-112                                        15.2     CN                                                                    15.3     OCH.sub.3                                                             15.4     NHSO.sub.2 CH.sub.3                                                   15.5     OC.sub.3 H.sub.7 (iso)                                                15.6     O-propargyl                                                           15.7     OCH(CH.sub.3)C.tbd.CH                                                 15.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        15.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          15.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 15.11    OCH.sub.2 COOCH.sub.3                                                 15.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     15.13    OCH.sub.2 COO-benzyl                                                  15.14    OCH(CH.sub.3)COObenzyl                                                15.15    SC.sub.3 H.sub.7 (iso)                                                15.16    SCH.sub.2 COOCH.sub.3                                                 15.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          15.18    SCH(CH.sub.3)COObenzyl                                                15.19    SCH.sub.2 COObenzyl                                                   15.20    COOCH.sub.3                                                           15.21    COOC.sub.3 H.sub.7 (iso)                                              15.22    COOC(CH.sub.3).sub.2 COOH                                             15.23    COOC(CH.sub.3).sub.2 COO-allyl                                        15.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      15.25    COOC(CH.sub.3).sub.2 COOethyl                                         15.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       15.27    CH.sub.2 CHClCOOethyl                                                 15.28    CH.sub.2 CH═CH.sub.2                                              15.29    CH.sub.2 CH.sub.2 CH.sub.3                                            15.30    CH.sub.2 CH.sub.2 CF.sub.3                                            15.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   15.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   15.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 15.34    CH.sub.2 CHClCOOH                                                     15.35    CH.sub.2 CHClCOOCH.sub.3                                              15.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 15.37    CH.sub.2 CHClCONHallyl                                                15.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            15.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     15.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           15.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          15.42    CH.sub.2 CH.sub.2 COOH                                                15.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         15.44    CH.sub.2 CH.sub.2 COOEt                                               15.45    CHClCHClCOOH                                                          15.46    CHClCHClCOOCH.sub.3                                                   15.47    CHClCHClCOOEt                                                         15.48    CH.sub.2 CH(OCH.sub.3)COOH                                            15.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     15.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           15.51    CH.sub.2 CH(SCH.sub.3)COOH                                            15.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     15.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           15.54    CH═CHCOOH                                                         15.55    CH═CHCOOCH.sub.3                                                  15.56    CH═CHCOOEt                                                        15.57    CH═CClCOOH                                                        15.58    CH═CClCOOCH.sub.3                                                 15.59    COOEt                                                                 15.60    CONH.sub.2                                                            15.61                                                                                    ##STR145##                                                           15.62    CONHSO.sub.2 CH.sub.3                                                 15.63    COOCH.sub.2 COOH                                                      15.64    COOCH.sub.2 COOCH.sub.3                                               15.65    COOCH(CH.sub.3)COOH                                                   15.66    COOCH(CH.sub.3)COOCH.sub.3                                            15.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          15.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   15.69    COOC(CH.sub.3).sub.2 CN                                               15.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        15.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   15.72                                                                                    ##STR146##                                                           15.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               15.74    COOCH.sub.2 C.tbd.CH                                                  15.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             15.76    COOCH(CH.sub.3)C.tbd.CH                                               15.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       15.78    NHallyl                                                               15.79    N(COCH.sub.3)allyl                                                    15.80    N(Et)SO.sub.2 CH.sub.3                                                15.81    N(allyl)SO.sub.2 CH.sub.3                                             15.82    N(allyl)SO.sub.2 Et                                                   15.83    SO.sub.2 N(CH.sub.3).sub.2                                            15.84    SO.sub.2 NH.sub.2                                                     15.85    SO.sub.2 NHCOCH.sub.3                                                 15.86    OH                                                                    15.87    OEt                                                                   15.88    Oallyl                                                                15.89    OCH.sub.2 C.tbd.CCH.sub.3                                             15.90    OCH(CH.sub.3)CH═CH.sub.2                                          15.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 15.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       15.93                                                                                    ##STR147##                                                           15.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         15.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              15.96    OCH.sub.2 CH.sub.2 COOH                                               15.97    OC(CH.sub.3).sub.2 COOH                                               15.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        15.99    OC(CH.sub.3).sub.2 COOEt                                              15.100   OCH.sub.2 COOH                                                        15.101   OSO.sub.2 CH.sub.3                                                    15.102   OSO.sub.2 CF.sub.3                                                    15.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       15.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               15.105   CH.sub.2 CHClCONHOH                                                   15.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              15.107   CH.sub.2 CH(CH.sub.3)COOH                                             15.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               15.109                                                                                   ##STR148##                                                           15.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            15.111                                                                                   ##STR149##                                                           15.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            15.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     15.114                                                                                   ##STR150##                                                           ______________________________________                                    

                                      TABLE 16                                     __________________________________________________________________________     Compounds of formula Iq                                                                                    (Iq)                                                ##STR151##                                                                    Comp.                                                                          No. R.sub.6     R.sub.4                                                                          R.sub.1                                                                           R.sub.2                                                                           R.sub.3                                                                              n  M.p.                                          __________________________________________________________________________     16.1                                                                               OCH.sub.3   Cl                                                                               Et Me Me    0                                                16.2                                                                               OCH.sub.3   Cl                                                                               Et Me Me    1                                                16.3                                                                               OCH.sub.3   Cl                                                                               Et Me Me    2                                                16.4                                                                               OCH.sub.3   F Et Me Me    0                                                16.5                                                                               OCH.sub.3   F Et Me Me    1                                                16.6                                                                               OCH.sub.3   F Et Me Me    2                                                16.7                                                                               H           Cl                                                                               Et Me Me    0  oil                                           16.8                                                                               H           Cl                                                                               Et Me Me    1  oil                                           16.9                                                                               H           Cl                                                                               Et Me Me    2  oil                                           16.10                                                                              H           F Et Me Me    0                                                16.11                                                                              H           F Et Me Me    1                                                16.12                                                                              H           F Et Me Me    2                                                16.13                                                                              O-propargyl Cl                                                                               Et Me Me    0                                                16.14                                                                              O-propargyl Cl                                                                               Et Me Me    1                                                16.15                                                                              O-propargyl Cl                                                                               Et Me Me    2                                                16.16                                                                              O-propargyl F Et Me Me    0                                                16.17                                                                              O-propargyl F Et Me Me    1                                                16.18                                                                              O-propargyl F Et Me Me    2                                                16.19                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Et Me Me    0                                                16.20                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Et Me Me    1                                                16.21                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Et Me Me    2                                                16.22                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Et Me Me    0                                                16.23                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Et Me Me    1                                                16.24                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Et Me Me    2                                                16.25                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Et Me Me    0  49-51                                         16.26                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Et Me Me    1  110-112                                       16.27                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Et Me Me    2  102-103                                       16.28                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Et Me Me    0                                                16.29                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Et Me Me    1                                                16.30                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Et Me Me    2                                                16.31                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Et Me Me    0                                                16.32                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Et Me Me    1                                                16.33                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Et Me Me    2                                                16.34                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Et Me Me    0                                                16.35                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Et Me Me    1                                                16.36                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Et Me Me    2                                                16.37                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Et Me Me    0                                                16.38                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Et Me Me    1                                                16.39                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Et Me Me    2                                                16.40                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Et Me Me    0                                                16.41                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Et Me Me    1                                                16.42                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Et Me Me    2                                                16.43                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Et Me Me    0                                                16.44                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Et Me Me    1                                                16.45                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Et Me Me    2                                                16.46                                                                              H           Cl                                                                               Me Me Et    0  48-50                                         16.47                                                                              H           Cl                                                                               Me Me Et    1  113-114                                       16.48                                                                              H           Cl                                                                               Me Me Et    2  101-103                                       16.49                                                                              H           F Me Me Et    0  oil                                           16.50                                                                              H           F Me Me Et    1  87-89                                         16.51                                                                              H           F Me Me Et    2  87-89                                         16.52                                                                              OCH.sub.3   Cl                                                                               Me Me Et    0                                                16.53                                                                              OCH.sub.3   Cl                                                                               Me Me Et    1                                                16.54                                                                              OCH.sub.3   Cl                                                                               Me Me Et    2                                                16.55                                                                              OCH.sub.3   F Me Me Et    0                                                16.56                                                                              OCH.sub.3   F Me Me Et    1                                                16.57                                                                              OCH.sub.3   F Me Me Et    2                                                16.58                                                                              O-propargyl Cl                                                                               Me Me Et    0                                                16.59                                                                              O-propargyl Cl                                                                               Me Me Et    1                                                16.60                                                                              O-propargyl Cl                                                                               Me Me Et    2                                                16.61                                                                              O-propargyl F Me Me Et    0  64-67                                         16.62                                                                              O-propargyl F Me Me Et    1                                                16.63                                                                              O-propargyl F Me Me Et    2  103-104                                       16.64                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me Et    0  57-60                                         16.65                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me Et    1  138-40                                        16.66                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me Et    2  70-72                                         16.67                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me Et    0                                                16.68                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me Et    1                                                16.69                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me Et    2                                                16.70                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me Et    0                                                16.71                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me Et    1                                                16.72                                                                              COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me Et    2                                                16.73                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me Et    0                                                16.74                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me Et    1                                                16.75                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me Et    2                                                16.76                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me Et    0                                                16.77                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me Et    1                                                16.78                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me Et    2                                                16.79                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me Et    0                                                16.80                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me Et    1                                                16.81                                                                              COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me Et    2                                                16.82                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me Et    0                                                16.83                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me Et    1                                                16.84                                                                              SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me Et    2                                                16.85                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Me Me Et    0                                                16.86                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Me Me Et    1                                                16.87                                                                              SCH.sub.2 COOCH.sub.3                                                                      F Me Me Et    2                                                16.88                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Me Me Et    0                                                16.89                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Me Me Et    1                                                16.90                                                                              SCH.sub.2 COOCH.sub.3                                                                      H Me Me Et    2                                                16.91                                                                              H           Cl                                                                               Me Me tert-butyl                                                                           0  oil                                           16.92                                                                              H           Cl                                                                               Me Me tert-butyl                                                                           1  93-94                                         16.93                                                                              H           Cl                                                                               Me Me tert-butyl                                                                           2  93-94                                         16.94                                                                              H           Cl                                                                               Me Me CHF.sub.2                                                                            0  solid                                         16.95                                                                              H           Cl                                                                               Me Me CHF.sub.2                                                                            1  78-79                                         16.96                                                                              H           Cl                                                                               Me Me CHF.sub.2                                                                            2  113-115                                       16.97                                                                              H           F Me Me CHF.sub.2                                                                            0                                                16.98                                                                              H           F Me Me CHF.sub.2                                                                            1                                                16.99                                                                              H           F Me Me CHF.sub.2                                                                            2                                                16.100                                                                             OCH.sub.3   Cl                                                                               Me Me CHF.sub.2                                                                            0                                                16.101                                                                             OCH.sub.3   Cl                                                                               Me Me CHF.sub.2                                                                            1                                                16.102                                                                             OCH.sub.3   Cl                                                                               Me Me CHF.sub.2                                                                            2                                                16.103                                                                             OCH.sub.3   F Me Me CHF.sub.2                                                                            0                                                16.104                                                                             OCH.sub.3   F Me Me CHF.sub.2                                                                            1                                                16.105                                                                             OCH.sub.3   F Me Me CHF.sub.2                                                                            2                                                16.106                                                                             O-propargyl Cl                                                                               Me Me CHF.sub.2                                                                            0                                                16.107                                                                             O-propargyl Cl                                                                               Me Me CHF.sub.2                                                                            1                                                16.108                                                                             O-propargyl Cl                                                                               Me Me CHF.sub.2                                                                            2                                                16.109                                                                             O-propargyl F Me Me CHF.sub.2                                                                            0                                                16.110                                                                             O-propargyl F Me Me CHF.sub.2                                                                            1                                                16.111                                                                             O-propargyl F Me Me CHF.sub.2                                                                            2                                                16.112                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CHF.sub.2                                                                            0                                                16.113                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CHF.sub.2                                                                            1                                                16.114                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CHF.sub.2                                                                            2                                                16.115                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CHF.sub.2                                                                            0                                                16.116                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CHF.sub.2                                                                            1                                                16.117                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CHF.sub.2                                                                            2                                                16.118                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CHF.sub.2                                                                            0                                                16.119                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CHF.sub.2                                                                            1                                                16.120                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CHF.sub.2                                                                            2                                                16.121                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CHF.sub.2                                                                            0                                                16.122                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CHF.sub.2                                                                            1                                                16.123                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CHF.sub.2                                                                            2                                                16.124                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CHF.sub.2                                                                            0                                                16.125                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CHF.sub.2                                                                            1                                                16.126                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CHF.sub.2                                                                            2                                                16.127                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CHF.sub.2                                                                            0                                                16.128                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CHF.sub.2                                                                            1                                                16.129                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CHF.sub.2                                                                            2                                                16.130                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CHF.sub.2                                                                            0                                                16.131                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CHF.sub.2                                                                            1                                                16.132                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CHF.sub.2                                                                            2                                                16.133                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CHF.sub.2                                                                            0                                                16.134                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CHF.sub.2                                                                            1                                                16.135                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CHF.sub.2                                                                            2                                                16.136                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CHF.sub.2                                                                            0                                                16.137                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CHF.sub.2                                                                            1                                                16.138                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CHF.sub.2                                                                            2                                                16.139                                                                             OCH.sub.3   Cl                                                                               Me Et Me    0                                                16.140                                                                             OCH.sub.3   Cl                                                                               Me Et Me    1                                                16.141                                                                             OCH.sub.3   Cl                                                                               Me Et Me    2                                                16.142                                                                             OCH.sub.3   F Me Et Me    0                                                16.143                                                                             OCH.sub.3   F Me Et Me    1                                                16.144                                                                             OCH.sub.3   F Me Et Me    2                                                16.145                                                                             H           Cl                                                                               Me Et Me    0  oil                                           16.146                                                                             H           Cl                                                                               Me Et Me    1  oil                                           16.147                                                                             H           Cl                                                                               Me Et Me    2  72-76                                         16.148                                                                             H           F Me Et Me    0                                                16.149                                                                             H           F Me Et Me    1                                                16.150                                                                             H           F Me Et Me    2                                                16.151                                                                             O-propargyl Cl                                                                               Me Et Me    0                                                16.152                                                                             O-propargyl Cl                                                                               Me Et Me    1                                                16.153                                                                             O-propargyl Cl                                                                               Me Et Me    2                                                16.154                                                                             O-propargyl F Me Et Me    0                                                16.155                                                                             O-propargyl F Me Et Me    1                                                16.156                                                                             O-propargyl F Me Et Me    2                                                16.157                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Et Me    0                                                16.158                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Et Me    1                                                16.159                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Et Me    2                                                16.160                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Et Me    0                                                16.161                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Et Me    1                                                16.162                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Et Me    2                                                16.163                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Et Me    0                                                16.164                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Et Me    1                                                16.165                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Et Me    2                                                16.166                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Et Me    0                                                16.167                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Et Me    1                                                16.168                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Et Me    2                                                16.169                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Et Me    0                                                16.170                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Et Me    1                                                16.171                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Et Me    2                                                16.172                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Et Me    0                                                16.173                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Et Me    1                                                16.174                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Et Me    2                                                16.175                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Et Me    0                                                16.176                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Et Me    1                                                16.177                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Et Me    2                                                16.178                                                                             CH.sub.2 CHClCOOH                                                                          F Me Et Me    0                                                16.179                                                                             CH.sub.2 CHClCOOH                                                                          F Me Et Me    1                                                16.180                                                                             CH.sub.2 CHClCOOH                                                                          F Me Et Me    2                                                16.181                                                                             CH.sub.2 CHClCOOH                                                                          H Me Et Me    0                                                16.182                                                                             CH.sub.2 CHClCOOH                                                                          H Me Et Me    1                                                16.183                                                                             CH.sub.2 CHClCOOH                                                                          H Me Et Me    2                                                16.184                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Et Me    0                                                16.185                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Et Me    1                                                16.186                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Et Me    2                                                16.187                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Et Me    0                                                16.188                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Et Me    1                                                16.189                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Et Me    2                                                16.190                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Et Me    0                                                16.191                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Et Me    1                                                16.192                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Et Me    2                                                16.193                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Et Me    0                                                16.194                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Et Me    1                                                16.195                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Et Me    2                                                16.196                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Et Me    0                                                16.197                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Et Me    1                                                16.198                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Et Me    2                                                16.199                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Et Me    0                                                16.200                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Et Me    1                                                16.201                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Et Me    2                                                16.202                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me Et    0                                                16.203                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me Et    1                                                16.204                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me Et    2                                                16.205                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me Et    0                                                16.206                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me Et    1                                                16.207                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me Et    2                                                16.208                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me Et    0                                                16.209                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me Et    1                                                16.210                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me Et    2                                                16.211                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me Et    0                                                16.212                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me Et    1                                                16.213                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me Et    2                                                16.214                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me Et    0                                                16.215                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me Et    1                                                16.216                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me Et    2                                                16.217                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me Et    0                                                16.218                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me Et    1                                                16.219                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me Et    2                                                16.220                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me Et    0                                                16.221                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me Et    1                                                16.222                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me Et    2                                                16.223                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me Et    0                                                16.224                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me Et    1                                                16.225                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me Et    2                                                16.226                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me Et    0                                                16.227                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me Et    1                                                16.228                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me Et    2                                                16.229                                                                             OCH.sub.2 COOEt                                                                            F Me Me ET    0                                                16.230                                                                             OCH.sub.2 COOEt                                                                            F Me Me Et    1                                                16.231                                                                             OCH.sub.2 COOEt                                                                            F Me Me Et    2                                                16.232                                                                             H           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.233                                                                             H           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.234                                                                             H           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.235                                                                             H           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.236                                                                             H           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.237                                                                             H           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.238                                                                             OCH.sub.3   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.239                                                                             OCH.sub.3   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.240                                                                             OCH.sub.3   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.241                                                                             OCH.sub.3   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.242                                                                             OCH.sub.3   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.243                                                                             OCH.sub.3   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.244                                                                             O-propargyl Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.245                                                                             O-propargyl Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.246                                                                             O-propargyl Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.247                                                                             O-propargyl F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.248                                                                             O-propargyl F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.249                                                                             O-propargyl F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.250                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.251                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.252                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.253                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.254                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.255                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.256                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.257                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.258                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.259                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.260                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.261                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.262                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.263                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.264                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.265                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.266                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.267                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.268                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.269                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.270                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.271                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.272                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.273                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.274                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.275                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.276                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.277                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.278                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.279                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.280                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.281                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.282                                                                             CH.sub.2 CHClCOOH                                                                          F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.283                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.284                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.285                                                                             CH.sub.2 CHClCOOH                                                                          H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.286                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.287                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.288                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.289                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.290                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.291                                                                             CH.sub.2 CHClCOOEt                                                                         F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.292                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.293                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.294                                                                             CH.sub.2 CHClCOOEt                                                                         H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.295                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.296                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.297                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   Cl                                                                               Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.298                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.299                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.300                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   F Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.301                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           0                                                16.302                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           1                                                16.303                                                                             CH.sub.2 CHClCOOCH.sub.3                                                                   H Me Me CH.sub.2 CH.sub.2 CH.sub.3                                                           2                                                16.304                                                                             OCH.sub.3   F Me Me CH.sub.2 CF.sub.3                                                                    0  oil                                           16.305                                                                             OCH.sub.3   F Me Me CH.sub.2 CF.sub.3                                                                    1                                                16.306                                                                             OCH.sub.3   F Me Me CH.sub.2 CF.sub.3                                                                    2                                                16.307                                                                             OCH.sub.3   Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.308                                                                             OCH.sub.3   Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.309                                                                             OCH.sub.3   Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.310                                                                             OCH.sub.3   F Me CHF.sub.2                                                                         Me    0                                                16.311                                                                             OCH.sub.3   F Me CHF.sub.2                                                                         Me    1                                                16.312                                                                             OCH.sub.3   F Me CHF.sub.2                                                                         Me    2                                                16.313                                                                             H           Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.314                                                                             H           Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.315                                                                             H           Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.316                                                                             H           F Me CHF.sub.2                                                                         Me    0                                                16.317                                                                             H           F Me CHF.sub.2                                                                         Me    1                                                16.318                                                                             H           F Me CHF.sub.2                                                                         Me    2                                                16.319                                                                             O-propargyl Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.320                                                                             O-propargyl Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.321                                                                             O-propargyl Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.322                                                                             O-propargyl F Me CHF.sub.2                                                                         Me    0                                                16.323                                                                             O-propargyl F Me CHF.sub.2                                                                         Me    1                                                16.324                                                                             O-propargyl F Me CHF.sub.2                                                                         Me    2                                                16.325                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.326                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.327                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.328                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CHF.sub.2                                                                         Me    0                                                16.329                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CHF.sub.2                                                                         Me    1                                                16.330                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CHF.sub.2                                                                         Me    2                                                16.331                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CHF.sub.2                                                                         Me    0                                                16.332                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CHF.sub.2                                                                         Me    1                                                16.333                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CHF.sub.2                                                                         Me    2                                                16.334                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.335                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.336                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.337                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CHF.sub.2                                                                         Me    0                                                16.338                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CHF.sub.2                                                                         Me    1                                                16.339                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CHF.sub.2                                                                         Me    2                                                16.340                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CHF.sub.2                                                                         Me    0                                                16.341                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CHF.sub.2                                                                         Me    1                                                16.342                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CHF.sub.2                                                                         Me    2                                                16.343                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.344                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.345                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.346                                                                             CH.sub.2 CHClCOOH                                                                          F Me CHF.sub.2                                                                         Me    0                                                16.347                                                                             CH.sub.2 CHClCOOH                                                                          F Me CHF.sub.2                                                                         Me    1                                                16.348                                                                             CH.sub.2 CHClCOOH                                                                          F Me CHF.sub.2                                                                         Me    2                                                16.349                                                                             CH.sub.2 CHClCOOH                                                                          H Me CHF.sub.2                                                                         Me    0                                                16.350                                                                             CH.sub.2 CHClCOOH                                                                          H Me CHF.sub.2                                                                         Me    1                                                16.351                                                                             CH.sub.2 CHClCOOH                                                                          H Me CHF.sub.2                                                                         Me    2                                                16.352                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.353                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.354                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.355                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CHF.sub.2                                                                         Me    0                                                16.356                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CHF.sub.2                                                                         Me    1                                                16.357                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CHF.sub.2                                                                         Me    2                                                16.358                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CHF.sub.2                                                                         Me    0                                                16.359                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CHF.sub.2                                                                         Me    1                                                16.360                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CHF.sub.2                                                                         Me    2                                                16.361                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CHF.sub.2                                                                         Me    0                                                16.362                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CHF.sub.2                                                                         Me    1                                                16.363                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CHF.sub.2                                                                         Me    2                                                16.364                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CHF.sub.2                                                                         Me    0                                                16.365                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CHF.sub.2                                                                         Me    1                                                16.366                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CHF.sub.2                                                                         Me    2                                                16.367                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CHF.sub.2                                                                         Me    0                                                16.368                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CHF.sub.2                                                                         Me    1                                                16.369                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CHF.sub.2                                                                         Me    2                                                16.370                                                                             OCH.sub.3   Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.371                                                                             OCH.sub.3   Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.372                                                                             OCH.sub.3   Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.373                                                                             OCH.sub.3   F Me CF.sub.3                                                                          Me    0                                                16.374                                                                             OCH.sub.3   F Me CF.sub.3                                                                          Me    1                                                16.375                                                                             OCH.sub.3   F Me CF.sub.3                                                                          Me    2                                                16.376                                                                             H           Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.377                                                                             H           Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.378                                                                             H           Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.379                                                                             H           F Me CF.sub.3                                                                          Me    0                                                16.380                                                                             H           F Me CF.sub.3                                                                          Me    1                                                16.381                                                                             H           F Me CF.sub.3                                                                          Me    2                                                16.382                                                                             O-propargyl Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.383                                                                             O-propargyl Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.384                                                                             O-propargyl Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.385                                                                             O-propargyl F Me CF.sub.3                                                                          Me    0                                                16.386                                                                             O-propargyl F Me CF.sub.3                                                                          Me    1                                                16.387                                                                             O-propargyl F Me CF.sub.3                                                                          Me    2                                                16.388                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.389                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.390                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.391                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CF.sub.3                                                                          Me    0                                                16.392                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CF.sub.3                                                                          Me    1                                                16.393                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   F Me CF.sub.3                                                                          Me    2                                                16.394                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CF.sub.3                                                                          Me    0                                                16.395                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CF.sub.3                                                                          Me    1                                                16.396                                                                             COOC.sub.3 H.sub.7 (iso)                                                                   H Me CF.sub.3                                                                          Me    2                                                16.397                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.398                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.399                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.400                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CF.sub.3                                                                          Me    0                                                16.401                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CF.sub.3                                                                          Me    1                                                16.402                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           F Me CF.sub.3                                                                          Me    2                                                16.403                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CF.sub.3                                                                          Me    0                                                16.404                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CF.sub.3                                                                          Me    1                                                16.405                                                                             COOC(CH.sub.3).sub.2 COOCH.sub.3                                                           H Me CF.sub.3                                                                          Me    2                                                16.406                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.407                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.408                                                                             CH.sub.2 CHClCOOH                                                                          Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.409                                                                             CH.sub.2 CHClCOOH                                                                          F Me CF.sub.3                                                                          Me    0                                                16.410                                                                             CH.sub.2 CHClCOOH                                                                          F Me CF.sub.3                                                                          Me    1                                                16.411                                                                             CH.sub.2 CHClCOOH                                                                          F Me CF.sub.3                                                                          Me    2                                                16.412                                                                             CH.sub.2 CHClCOOH                                                                          H Me CF.sub.3                                                                          Me    0                                                16.413                                                                             CH.sub.2 CHClCOOH                                                                          H Me CF.sub.3                                                                          Me    1                                                16.414                                                                             CH.sub.2 CHClCOOH                                                                          H Me CF.sub.3                                                                          Me    2                                                16.415                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.416                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.417                                                                             CH.sub.2 CHClCOOEt                                                                         Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.418                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CF.sub.3                                                                          Me    0                                                16.419                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CF.sub.3                                                                          Me    1                                                16.420                                                                             CH.sub.2 CHClCOOEt                                                                         F Me CF.sub.3                                                                          Me    2                                                16.421                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CF.sub.3                                                                          Me    0                                                16.422                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CF.sub.3                                                                          Me    1                                                16.423                                                                             CH.sub.2 CHClCOOEt                                                                         H Me CF.sub.3                                                                          Me    2                                                16.424                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CF.sub.3                                                                          Me    0                                                16.425                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CF.sub.3                                                                          Me    1                                                16.426                                                                             SCH.sub.2 COOCH.sub.3                                                                      Cl                                                                               Me CF.sub.3                                                                          Me    2                                                16.427                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CF.sub.3                                                                          Me    0                                                16.428                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CF.sub.3                                                                          Me    1                                                16.429                                                                             SCH.sub.2 COOCH.sub.3                                                                      F Me CF.sub.3                                                                          Me    2                                                16.430                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CF.sub.3                                                                          Me    0                                                16.431                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CF.sub.3                                                                          Me    1                                                16.432                                                                             SCH.sub.2 COOCH.sub.3                                                                      H Me CF.sub.3                                                                          Me    2                                                16.433                                                                             H           H Et Me Me    0  35-38                                         16.434                                                                             NH.sub.2    Cl                                                                               Me Me Et    0  82-83                                         16.435                                                                             I           H Et Me Me    0  78-80                                         __________________________________________________________________________

                  TABLE 17                                                         ______________________________________                                         Compounds of formula Ir                                                                                       (Ir)                                             ##STR152##                                                                    Comp.                                                                          No.    R.sub.6        R.sub.4 R.sub.5                                                                             n    M.p.                                   ______________________________________                                         17.1   H              CH.sub.3                                                                               CH.sub.3                                                                            0                                           17.2   H              CH.sub.3                                                                               CH.sub.3                                                                            1                                           17.3   H              CH.sub.3                                                                               CH.sub.3                                                                            2                                           17.4   H              F       CF.sub.3                                                                            0    oil                                    17.5   H              F       CF.sub.3                                                                            1    112-120                                17.6   H              F       CF.sub.3                                                                            2    121-123                                17.7   H              Cl      F    0    oil                                    17.8   H              Cl      F    1     99-101                                17.9   H              Cl      F    2    85-87                                  17.10  H              F       F    0    solid                                  17.11  H              F       F    1    solid                                  17.12  H              F       F    2                                           17.13  COOC(CH.sub.3).sub.2 COOH                                                                     H       H    0                                           17.14  COOC(CH.sub.3).sub.2 COOH                                                                     H       H    1                                           17.15  COOC(CH.sub.3).sub.2 COOH                                                                     H       H    2    139-143                                17.16  COOC(CH.sub.3).sub.2 COOCH.sub.3                                                              H       H    0                                           17.17  COOC(CH.sub.3).sub.2 COOCH.sub.3                                                              H       H    1                                           17.18  COOC(CH.sub.3).sub.2 COOCH.sub.3                                                              H       H    2    oil                                    17.19  H              Br      Cl   0    84-88                                  17.20  H              Br      Cl   1    91-93                                  17.21  H              Br      Cl   2    123-124                                ______________________________________                                    

                  TABLE 18                                                         ______________________________________                                         Compounds of formula Is                                                                                       (Is)                                             ##STR153##                                                                    Comp.                                                                          No.    R.sub.6  R.sub.5 R.sub.4                                                                             R.sub.1                                                                              R.sub.2                                                                               M.p.                                 ______________________________________                                         18.1   H        F       Cl   CH.sub.3                                                                             SCH.sub.3                                                                             oil                                  18.2   H        Cl      F    CH.sub.3                                                                             SCH.sub.3                                                                             88-90                                18.3   OCH.sub.3                                                                               Cl      F    CH.sub.3                                                                             SCH.sub.3                                                                              98-100                              18.4   H        Cl      Cl   CH.sub.3                                                                             SCH.sub.3                                                                             oil                                  18.5   OCH.sub.3                                                                               Cl      F    CH.sub.3                                                                             SOCH.sub.3                                                                            171-173                              18.6   NO.sub.2 Cl      F    CH.sub.3                                                                             SOCH.sub.3                                                                            solid                                18.7   H        Cl      F    CH.sub.3                                                                             SOCH.sub.3                                                                            solid                                18.8   H        CF.sub.3                                                                               F    CH.sub.3                                                                             SCH.sub.3                                                                             solid                                ______________________________________                                    

                  TABLE 19                                                         ______________________________________                                         Compounds of formula It                                                                                       (It)                                             ##STR154##                                                                    Comp. No.                                                                               R.sub.6                  M.p.                                         ______________________________________                                         19.1     H                                                                     19.2     CN                                                                    19.3     OCH.sub.3                                                             19.4     NHSO.sub.2 CH.sub.3                                                   19.5     OC.sub.3 H.sub.7 (iso)                                                19.6     O-propargyl                                                           19.7     OCH(CH.sub.3)C.tbd.CH                                                 19.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        19.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          19.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 19.11    OCH.sub.2 COOCH.sub.3                                                 19.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     19.13    OCH.sub.2 COO-benzyl                                                  19.14    OCH(CH.sub.3)COObenzyl                                                19.15    SC.sub.3 H.sub.7 (iso)                                                19.16    SCH.sub.2 COOCH.sub.3                                                 19.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          19.18    SCH(CH.sub.3)COObenzyl                                                19.19    SCH.sub.2 COObenzyl                                                   19.20    COOCH.sub.3                                                           19.21    COOC.sub.3 H.sub.7 (iso)                                              19.22    COOC(CH.sub.3).sub.2 COOH                                             19.23    COOC(CH.sub.3).sub.2 COO-allyl                                        19.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      19.25    COOC(CH.sub.3).sub.2 COOethyl                                         19.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       19.27    CH.sub.2 CHClCOOethyl                                                 19.28    CH.sub.2 CH═CH.sub.2                                              19.29    CH.sub.2 CH.sub.2 CH.sub.3                                            19.30    CH.sub.2 CH.sub.2 CF.sub.3                                            19.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   19.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   19.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 19.34    CH.sub.2 CHClCOOH                                                     19.35    CH.sub.2 CHClCOOCH.sub.3                                              19.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 19.37    CH.sub.2 CHClCONHallyl                                                19.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            19.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     19.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           19.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          19.42    CH.sub.2 CH.sub.2 COOH                                                19.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         19.44    CH.sub.2 CH.sub.2 COOEt                                               19.45    CHClCHClCOOH                                                          19.46    CHClCHClCOOCH.sub.3                                                   19.47    CHClCHClCOOEt                                                         19.48    CH.sub.2 CH(OCH.sub.3)COOH                                            19.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     19.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           19.51    CH.sub.2 CH(SCH.sub.3)COOH                                            19.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     19.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           19.54    CH═CHCOOH                                                         19.55    CH═CHCOOCH.sub.3                                                  19.56    CH═CHCOOEt                                                        19.57    CH═CClCOOH                                                        19.58    CH═CClCOOCH.sub.3                                                 19.59    COOEt                                                                 19.60    CONH.sub.2                                                            19.61                                                                                    ##STR155##                                                           19.62    CONHSO.sub.2 CH.sub.3                                                 19.63    COOCH.sub.2 COOH                                                      19.64    COOCH.sub.2 COOCH.sub.3                                               19.65    COOCH(CH.sub.3)COOH                                                   19.66    COOCH(CH.sub.3)COOCH.sub.3                                            19.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          19.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   19.69    COOC(CH.sub.3).sub.2 CN                                               19.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        19.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   19.72                                                                                    ##STR156##                                                           19.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               19.74    COOCH.sub.2 C.tbd.CH                                                  19.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             19.76    COOCH(CH.sub.3)C.tbd.CH                                               19.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       19.78    NHallyl                                                               19.79    N(COCH.sub.3)allyl                                                    19.80    N(Et)SO.sub.2 CH.sub.3                                                19.81    N(allyl)SO.sub.2 CH.sub.3                                             19.82    N(allyl)SO.sub.2 Et                                                   19.83    SO.sub.2 N(CH.sub.3).sub.2                                            19.84    SO.sub.2 NH.sub.2                                                     19.85    SO.sub.2 NHCOCH.sub.3                                                 19.86    OH                                                                    19.87    OEt                                                                   19.88    Oallyl                                                                19.89    OCH.sub.2 C.tbd.CCH.sub.3                                             19.90    OCH(CH.sub.3)CH═CH.sub.2                                          19.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 19.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       19.93                                                                                    ##STR157##                                                           19.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         19.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              19.96    OCH.sub.2 CH.sub.2 COOH                                               19.97    OC(CH.sub.3).sub.2 COOH                                               19.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        19.99    OC(CH.sub.3).sub.2 COOEt                                               19.100  OCH.sub.2 COOH                                                         19.101  OSO.sub.2 CH.sub.3                                                     19.102  OSO.sub.2 CF.sub.3                                                     19.103  CH.sub.2 CHClCOOC.sub.2 H.sub.5                                        19.104  CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                                19.105  CH.sub.2 CHClCONHOH                                                    19.106  CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                               19.107  CH.sub.2 CH(CH.sub.3)COOH                                              19.108  CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                                19.109                                                                                  ##STR158##                                                            19.110  COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             19.111                                                                                  ##STR159##                                                            19.112  COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                             19.113  COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                      19.114                                                                                  ##STR160##                                                           ______________________________________                                    

                  TABLE 20                                                         ______________________________________                                         Compounds of formula Iu                                                                                      (Iu)                                              ##STR161##                                                                    Comp. No.                                                                               R.sub.6                  M.p.                                         ______________________________________                                         20.1     H                                                                     20.2     CN                                                                    20.3     OCH.sub.3                                                             20.4     NHSO.sub.2 CH.sub.3                                                   20.5     OC.sub.3 H.sub.7 (iso)                                                20.6     O-propargyl                                                           20.7     OCH(CH.sub.3)C.tbd.CH                                                 20.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        20.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          20.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 20.11    OCH.sub.2 COOCH.sub.3                                                 20.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     20.13    OCH.sub.2 COO-benzyl                                                  20.14    OCH(CH.sub.3)COObenzyl                                                20.15    SC.sub.3 H.sub.7 (iso)                                                20.16    SCH.sub.2 COOCH.sub.3                                                 20.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          20.18    SCH(CH.sub.3)COObenzyl                                                20.19    SCH.sub.2 COObenzyl                                                   20.20    COOCH.sub.3                                                           20.21    COOC.sub.3 H.sub.7 (iso)                                              20.22    COOC(CH.sub.3).sub.2 COOH                                             20.23    COOC(CH.sub.3).sub.2 COO-allyl                                        20.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      20.25    COOC(CH.sub.3).sub.2 COOethyl                                         20.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       20.27    CH.sub.2 CHClCOOethyl                                                 20.28    CH.sub.2 CH═CH.sub.2                                              20.29    CH.sub.2 CH.sub.2 CH.sub.3                                            20.30    CH.sub.2 CH.sub.2 CF.sub.3                                            20.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   20.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   20.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 20.34    CH.sub.2 CHClCOOH                                                     20.35    CH.sub.2 CHClCOOCH.sub.3                                              20.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 20.37    CH.sub.2 CHClCONHallyl                                                20.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            20.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     20.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           20.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          20.42    CH.sub.2 CH.sub.2 COOH                                                20.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         20.44    CH.sub.2 CH.sub.2 COOEt                                               20.45    CHClCHClCOOH                                                          20.46    CHClCHClCOOCH.sub.3                                                   20.47    CHClCHClCOOEt                                                         20.48    CH.sub.2 CH(OCH.sub.3)COOH                                            20.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     20.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           20.51    CH.sub.2 CH(SCH.sub.3)COOH                                            20.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     20.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           20.54    CH═CHCOOH                                                         20.55    CH═CHCOOCH.sub.3                                                  20.56    CH═CHCOOEt                                                        20.57    CH═CClCOOH                                                        20.58    CH═CClCOOCH.sub.3                                                 20.59    COOEt                                                                 20.60    CONH.sub.2                                                            20.61                                                                                    ##STR162##                                                           20.62    CONHSO.sub.2 CH.sub.3                                                 20.63    COOCH.sub.2 COOH                                                      20.64    COOCH.sub.2 COOCH.sub.3                                               20.65    COOCH(CH.sub.3)COOH                                                   20.66    COOCH(CH.sub.3)COOCH.sub.3                                            20.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          20.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   20.69    COOC(CH.sub.3).sub.2 CN                                               20.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        20.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   20.72                                                                                    ##STR163##                                                           20.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               20.74    COOCH.sub.2 C.tbd.CH                                                  20.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             20.76    COOCH(CH.sub.3)C.tbd.CH                                               20.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       20.78    NHallyl                                                               20.79    N(COCH.sub.3)allyl                                                    20.80    N(Et)SO.sub.2 CH.sub.3                                                20.81    N(allyl)SO.sub.2 CH.sub.3                                             20.82    N(allyl)SO.sub.2 Et                                                   20.83    SO.sub.2 N(CH.sub.3).sub.2                                            20.84    SO.sub.2 NH.sub.2                                                     20.85    SO.sub.2 NHCOCH.sub.3                                                 20.86    OH                                                                    20.87    OEt                                                                   20.88    Oallyl                                                                20.89    OCH.sub.2 C.tbd.CCH.sub.3                                             20.90    OCH(CH.sub.3)CH═CH.sub.2                                          20.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 20.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       20.93                                                                                    ##STR164##                                                           20.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         20.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              20.96    OCH.sub.2 CH.sub.2 COOH                                               20.97    OC(CH.sub.3).sub.2 COOH                                               20.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        20.99    OC(CH.sub.3).sub.2 COOEt                                               20.100  OCH.sub.2 COOH                                                         20.101  OSO.sub.2 CH.sub.3                                                     20.102  OSO.sub.2 CF.sub.3                                                     20.103  CH.sub.2 CHClCOOC.sub.2 H.sub.5                                        20.104  CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                                20.105  CH.sub.2 CHClCONHOH                                                    20.106  CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                               20.107  CH.sub.2 CH(CH.sub.3)COOH                                              20.108  CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                                20.109                                                                                  ##STR165##                                                            20.110  COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             20.111                                                                                  ##STR166##                                                            20.112  COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                             20.113  COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                      20.114                                                                                  ##STR167##                                                           ______________________________________                                    

                  TABLE 21                                                         ______________________________________                                         Compounds of formula Iv                                                                                      (Iv)                                              ##STR168##                                                                    Comp. No.                                                                               R.sub.6                  M.p.                                         ______________________________________                                         21.1     H                                                                     21.2     CN                                                                    21.3     OCH.sub.3                                                             21.4     NHSO.sub.2 CH.sub.3                                                   21.5     OC.sub.3 H.sub.7 (iso)                                                21.6     O-propargyl                                                           21.7     OCH(CH.sub.3)C.tbd.CH                                                 21.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        21.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          21.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 21.11    OCH.sub.2 COOCH.sub.3                                                 21.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     21.13    OCH.sub.2 COO-benzyl                                                  21.14    OCH(CH.sub.3)COObenzyl                                                21.15    SC.sub.3 H.sub.7 (iso)                                                21.16    SCH.sub.2 COOCH.sub.3                                                 21.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          21.18    SCH(CH.sub.3)COObenzyl                                                21.19    SCH.sub.2 COObenzyl                                                   21.20    COOCH.sub.3                                                           21.21    COOC.sub.3 H.sub.7 (iso)                                              21.22    COOC(CH.sub.3).sub.2 COOH                                             21.23    COOC(CH.sub.3).sub.2 COO-allyl                                        21.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      21.25    COOC(CH.sub.3).sub.2 COOethyl                                         21.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       21.27    CH.sub.2 CHClCOOethyl                                                 21.28    CH.sub.2 CH═CH.sub.2                                              21.29    CH.sub.2 CH.sub.2 CH.sub.3                                            21.30    CH.sub.2 CH.sub.2 CF.sub.3                                            21.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   21.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   21.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 21.34    CH.sub.2 CHClCOOH                                                     21.35    CH.sub.2 CHClCOOCH.sub.3                                              21.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 21.37    CH.sub.2 CHClCONHallyl                                                21.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            21.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     21.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           21.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          21.42    CH.sub.2 CH.sub.2 COOH                                                21.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         21.44    CH.sub.2 CH.sub.2 COOEt                                               21.45    CHClCHClCOOH                                                          21.46    CHClCHClCOOCH.sub.3                                                   21.47    CHClCHClCOOEt                                                         21.48    CH.sub.2 CH(OCH.sub.3)COOH                                            21.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     21.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           21.51    CH.sub.2 CH(SCH.sub.3)COOH                                            21.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     21.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           21.54    CH═CHCOOH                                                         21.55    CH═CHCOOCH.sub.3                                                  21.56    CH═CHCOOEt                                                        21.57    CH═CClCOOH                                                        21.58    CH═CClCOOCH.sub.3                                                 21.59    COOEt                                                                 21.60    CONH.sub.2                                                            21.61                                                                                    ##STR169##                                                           21.62    CONHSO.sub.2 CH.sub.3                                                 21.63    COOCH.sub.2 COOH                                                      21.64    COOCH.sub.2 COOCH.sub.3                                               21.65    COOCH(CH.sub.3)COOH                                                   21.66    COOCH(CH.sub.3)COOCH.sub.3                                            21.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          21.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   21.69    COOC(CH.sub.3).sub.2 CN                                               21.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        21.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   21.72                                                                                    ##STR170##                                                           21.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               21.74    COOCH.sub.2 C.tbd.CH                                                  21.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             21.76    COOCH(CH.sub.3)C.tbd.CH                                               21.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       21.78    NHallyl                                                               21.79    N(COCH.sub.3)allyl                                                    21.80    N(Et)SO.sub.2 CH.sub.3                                                21.81    N(allyl)SO.sub.2 CH.sub.3                                             21.82    N(allyl)SO.sub.2 Et                                                   21.83    SO.sub.2 N(CH.sub.3).sub.2                                            21.84    SO.sub.2 NH.sub.2                                                     21.85    SO.sub.2 NHCOCH.sub.3                                                 21.86    OH                                                                    21.87    OEt                                                                   21.88    Oallyl                                                                21.89    OCH.sub.2 C.tbd.CCH.sub.3                                             21.90    OCH(CH.sub.3)CH═CH.sub.2                                          21.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 21.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       21.93                                                                                    ##STR171##                                                           21.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         21.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              21.96    OCH.sub.2 CH.sub.2 COOH                                               21.97    OC(CH.sub.3).sub.2 COOH                                               21.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        21.99    OC(CH.sub.3).sub.2 COOEt                                               21.100  OCH.sub.2 COOH                                                         21.101  OSO.sub.2 CH.sub.3                                                     21.102  OSO.sub.2 CF.sub.3                                                     21.103  CH.sub.2 CHClCOOC.sub.2 H.sub.5                                        21.104  CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                                21.105  CH.sub.2 CHClCONHOH                                                    21.106  CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                               21.107  CH.sub.2 CH(CH.sub.3)COOH                                              21.108  CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                                21.109                                                                                  ##STR172##                                                            21.110  COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             21.111                                                                                  ##STR173##                                                            21.112  COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                             21.113  COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                      21.114                                                                                  ##STR174##                                                           ______________________________________                                    

                  TABLE 22                                                         ______________________________________                                         Compounds of formula lw                                                         ##STR175##                   (lw)                                             Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         22.1     H                                                                     22.2     CN                                                                    22.3     OCH.sub.3                                                             22.4     NHSO.sub.2 CH.sub.3                                                   22.5     OC.sub.3 H.sub.7 (iso)                                                22.6     O-propargyl                                                           22.7     OCH(CH.sub.3)C.tbd.CH                                                 22.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        22.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          22.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 22.11    OCH.sub.2 COOCH.sub.3                                                 22.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     22.13    OCH.sub.2 COO-benzyl                                                  22.14    OCH(CH.sub.3)COObenzyl                                                22.15    SC.sub.3 H.sub.7 (iso)                                                22.16    SCH.sub.2 COOCH.sub.3                                                 22.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          22.18    SCH(CH.sub.3)COObenzyl                                                22.19    SCH.sub.2 COObenzyl                                                   22.20    COOCH.sub.3                                                           22.21    COOC.sub.3 H.sub.7 (iso)                                              22.22    COO(CH.sub.3).sub.2 COOH                                              22.23    COOC(CH.sub.3).sub.2 COO-allyl                                        22.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      22.25    COO(CH.sub.3).sub.2 COOethyl                                          22.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       22.27    CH.sub.2 CHClCOOethyl                                                 22.28    CH.sub.2 CH═CH.sub.2                                              22.29    CH.sub.2 CH.sub.2 CH.sub.3                                            22.30    CH.sub.2 CH.sub.2 CF.sub.3                                            22.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   22.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   22.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 22.34    CH.sub.2 CHClCOOH                                                     22.35    CH.sub.2 CHClCOOCH.sub.3                                              22.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 22.37    CH.sub.2 CHClCONHallyl                                                22.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            22.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     22.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           22.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          22.42    CH.sub.2 CH.sub.2 COOH                                                22.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         22.44    CH.sub.2 CH.sub.2 COOEt                                               22.45    CHClCHClCOOH                                                          22.46    CHClCHClCOOCH.sub.3                                                   22.47    CHClCHClCOOEt                                                         22.48    CH.sub.2 CH(OCH.sub.3)COOH                                            22.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     22.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           22.51    CH.sub.2 CH(SCH.sub.3)COOH                                            22.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     22.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           22.54    CH═CHCOOH                                                         22.55    CH═CHCOOCH.sub.3                                                  22.56    CH═CHCOOEt                                                        22.57    CH═CClCOOH                                                        22.58    CH═CClCOOCH.sub.3                                                 22.59    COOEt                                                                 22.60    CONH.sub.2                                                            22.61                                                                                    ##STR176##                                                           22.62    CONHSO.sub.2 CH.sub.3                                                 22.63    COOCH.sub.2 COOH                                                      22.64    COOCH.sub.2 COOCH.sub.3                                               22.65    COOCH(CH.sub.3)COOH                                                   22.66    COOCH(CH.sub.3)COOCH.sub.3                                            22.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          22.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   22.69    COOC(CH.sub.3).sub.2 CN                                               22.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        22.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   22.72                                                                                    ##STR177##                                                           22.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               22.74    COOCH.sub.2 C.tbd.CH                                                  22.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             22.76    COOCH(CH.sub.3)C.tbd.CH                                               22.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       22.78    NHallyl                                                               22.79    N(COCH.sub.3)allyl                                                    22.80    N(Et)SO.sub.2 CH.sub.3                                                22.81    N(allyl)SO.sub.2 CH.sub.3                                             22.82    N(allyl)SO.sub.2 Et                                                   22.83    SO.sub.2 N(CH.sub.3).sub.2                                            22.84    SO.sub.2 NH.sub.2                                                     22.85    SO.sub.2 NHCOCH.sub.3                                                 22.86    OH                                                                    22.87    OEt                                                                   22.88    Oallyl                                                                22.89    OCH.sub.2 C.tbd.CCH.sub.3                                             22.90    OCH(CH.sub.3)CH═CH.sub.2                                          22.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 22.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       22.93                                                                                    ##STR178##                                                           22.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         22.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              22.96    OCH.sub.2 CH.sub.2 COOH                                               22.97    OC(CH.sub.3).sub.2 COOH                                               22.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        22.99    OC(CH.sub.3).sub.2 COOEt                                              22.100   OCH.sub.2 COOH                                                        22.101   OSO.sub.2 CH.sub.3                                                    22.102   OSO.sub.2 CF.sub.3                                                    22.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       22.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               22.105   CH.sub.2 CHClCONHOH                                                   22.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              22.107   CH.sub.2 CH(CH.sub.3)COOH                                             22.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               22.109                                                                                   ##STR179##                                                           22.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            22.111                                                                                   ##STR180##                                                           22.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            22.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     22.114                                                                                   ##STR181##                                                           ______________________________________                                    

                  TABLE 23                                                         ______________________________________                                         Compounds of formula lx                                                         ##STR182##                   (lx)                                             Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         23.1     H                                                                     23.2     CN                                                                    23.3     OCH.sub.3                                                             23.4     NHSO.sub.2 CH.sub.3                                                   23.5     OC.sub.3 H.sub.7 (iso)                                                23.6     O-propargyl                                                           23.7     OCH(CH.sub.3)C.tbd.CH                                                 23.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        23.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          23.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 23.11    OCH.sub.2 COOCH.sub.3                                                 23.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     23.13    OCH.sub.2 COO-benzyl                                                  23.14    OCH(CH.sub.3)COObenzyl                                                23.15    SC.sub.3 H.sub.7 (iso)                                                23.16    SCH.sub.2 COOCH.sub.3                                                 23.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          23.18    SCH(CH.sub.3)COObenzyl                                                23.19    SCH.sub.2 COObenzyl                                                   23.20    COOCH.sub.3                                                           23.21    COOC.sub.3 H.sub.7 (iso)                                              23.22    COO(CH.sub.3).sub.2 COOH                                              23.23    COOC(CH.sub.3).sub.2 COO-allyl                                        23.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      23.25    COO(CH.sub.3).sub.2 COOethyl                                          23.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       23.27    CH.sub.2 CHClCOOethyl                                                 23.28    CH.sub.2 CH═CH.sub.2                                              23.29    CH.sub.2 CH.sub.2 CH.sub.3                                            23.30    CH.sub.2 CH.sub.2 CF.sub.3                                            23.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   23.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   23.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 23.34    CH.sub.2 CHClCOOH                                                     23.35    CH.sub.2 CHClCOOCH.sub.3                                              23.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 23.37    CH.sub.2 CHClCONHallyl                                                23.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            23.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     23.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           23.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          23.42    CH.sub.2 CH.sub.2 COOH                                                23.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         23.44    CH.sub.2 CH.sub.2 COOEt                                               23.45    CHClCHClCOOH                                                          23.46    CHClCHClCOOCH.sub.3                                                   23.47    CHClCHClCOOEt                                                         23.48    CH.sub.2 CH(OCH.sub.3)COOH                                            23.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     23.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           23.51    CH.sub.2 CH(SCH.sub.3)COOH                                            23.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     23.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           23.54    CH═CHCOOH                                                         23.55    CH═CHCOOCH.sub.3                                                  23.56    CH═CHCOOEt                                                        23.57    CH═CClCOOH                                                        23.58    CH═CClCOOCH.sub.3                                                 23.59    COOEt                                                                 23.60    CONH.sub.2                                                            23.61                                                                                    ##STR183##                                                           23.62    CONHSO.sub.2 CH.sub.3                                                 23.63    COOCH.sub.2 COOH                                                      23.64    COOCH.sub.2 COOCH.sub.3                                               23.65    COOCH(CH.sub.3)COOH                                                   23.66    COOCH(CH.sub.3)COOCH.sub.3                                            23.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          23.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   23.69    COOC(CH.sub.3).sub.2 CN                                               23.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        23.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   23.72                                                                                    ##STR184##                                                           23.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               23.74    COOCH.sub.2 C.tbd.CH                                                  23.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             23.76    COOCH(CH.sub.3)C.tbd.CH                                               23.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       23.78    NHallyl                                                               23.79    N(COCH.sub.3)allyl                                                    23.80    N(Et)SO.sub.2 CH.sub.3                                                23.81    N(allyl)SO.sub.2 CH.sub.3                                             23.82    N(allyl)SO.sub.2 Et                                                   23.83    SO.sub.2 N(CH.sub.3).sub.2                                            23.84    SO.sub.2 NH.sub.2                                                     23.85    SO.sub.2 NHCOCH.sub.3                                                 23.86    OH                                                                    23.87    OEt                                                                   23.88    Oallyl                                                                23.89    OCH.sub.2 C.tbd.CCH.sub.3                                             23.90    OCH(CH.sub.3)CH═CH.sub.2                                          23.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 23.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       23.93                                                                                    ##STR185##                                                           23.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         23.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              23.96    OCH.sub.2 CH.sub.2 COOH                                               23.97    OC(CH.sub.3).sub.2 COOH                                               23.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        23.99    OC(CH.sub.3).sub.2 COOEt                                              23.100   OCH.sub.2 COOH                                                        23.101   OSO.sub.2 CH.sub.3                                                    23.102   OSO.sub.2 CF.sub.3                                                    23.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       23.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               23.105   CH.sub.2 CHClCONHOH                                                   23.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              23.107   CH.sub.2 CH(CH.sub.3)COOH                                             23.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               23.109                                                                                   ##STR186##                                                           23.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            23.111                                                                                   ##STR187##                                                           23.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            23.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     23.114                                                                                   ##STR188##                                                           ______________________________________                                    

                  TABLE 24                                                         ______________________________________                                         Compounds of formula ly                                                         ##STR189##                   (ly)                                             Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         24.1     H                                                                     24.2     CN                                                                    24.3     OCH.sub.3                                                             24.4     NHSO.sub.2 CH.sub.3                                                   24.5     OC.sub.3 H.sub.7 (iso)                                                24.6     O-propargyl                                                           24.7     OCH(CH.sub.3)C.tbd.CH                                                 24.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        24.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          24.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 24.11    OCH.sub.2 COOCH.sub.3                                                 24.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     24.13    OCH.sub.2 COO-benzyl                                                  24.14    OCH(CH.sub.3)COObenzyl                                                24.15    SC.sub.3 H.sub.7 (iso)                                                24.16    SCH.sub.2 COOCH.sub.3                                                 24.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          24.18    SCH(CH.sub.3)COObenzyl                                                24.19    SCH.sub.2 COObenzyl                                                   24.20    COOCH.sub.3                                                           24.21    COOC.sub.3 H.sub.7 (iso)                                              24.22    COO(CH.sub.3).sub.2 COOH                                              24.23    COOC(CH.sub.3).sub.2 COO-allyl                                        24.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      24.25    COO(CH.sub.3).sub.2 COOethyl                                          24.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       24.27    CH.sub.2 CHClCOOethyl                                                 24.28    CH.sub.2 CH═CH.sub.2                                              24.29    CH.sub.2 CH.sub.2 CH.sub.3                                            24.30    CH.sub.2 CH.sub.2 CF.sub.3                                            24.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   24.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   24.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 24.34    CH.sub.2 CHClCOOH                                                     24.35    CH.sub.2 CHClCOOCH.sub.3                                              24.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 24.37    CH.sub.2 CHClCONHallyl                                                24.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            24.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     24.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           24.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          24.42    CH.sub.2 CH.sub.2 COOH                                                24.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         24.44    CH.sub.2 CH.sub.2 COOEt                                               24.45    CHClCHClCOOH                                                          24.46    CHClCHClCOOCH.sub.3                                                   24.47    CHClCHClCOOEt                                                         24.48    CH.sub.2 CH(OCH.sub.3)COOH                                            24.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     24.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           24.51    CH.sub.2 CH(SCH.sub.3)COOH                                            24.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     24.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           24.54    CH═CHCOOH                                                         24.55    CH═CHCOOCH.sub.3                                                  24.56    CH═CHCOOEt                                                        24.57    CH═CClCOOH                                                        24.58    CH═CClCOOCH.sub.3                                                 24.59    COOEt                                                                 24.60    CONH.sub.2                                                            24.61                                                                                    ##STR190##                                                           24.62    CONHSO.sub.2 CH.sub.3                                                 24.63    COOCH.sub.2 COOH                                                      24.64    COOCH.sub.2 COOCH.sub.3                                               24.65    COOCH(CH.sub.3)COOH                                                   24.66    COOCH(CH.sub.3)COOCH.sub.3                                            24.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          24.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   24.69    COOC(CH.sub.3).sub.2 CN                                               24.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        24.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   24.72                                                                                    ##STR191##                                                           24.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               24.74    COOCH.sub.2 C.tbd.CH                                                  24.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             24.76    COOCH(CH.sub.3)C.tbd.CH                                               24.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       24.78    NHallyl                                                               24.79    N(COCH.sub.3)allyl                                                    24.80    N(Et)SO.sub.2 CH.sub.3                                                24.81    N(allyl)SO.sub.2 CH.sub.3                                             24.82    N(allyl)SO.sub.2 Et                                                   24.83    SO.sub.2 N(CH.sub.3).sub.2                                            24.84    SO.sub.2 NH.sub.2                                                     24.85    SO.sub.2 NHCOCH.sub.3                                                 24.86    OH                                                                    24.87    OEt                                                                   24.88    Oallyl                                                                24.89    OCH.sub.2 C.tbd.CCH.sub.3                                             24.90    OCH(CH.sub.3)CH═CH.sub.2                                          24.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 24.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       24.93                                                                                    ##STR192##                                                           24.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         24.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              24.96    OCH.sub.2 CH.sub.2 COOH                                               24.97    OC(CH.sub.3).sub.2 COOH                                               24.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        24.99    OC(CH.sub.3).sub.2 COOEt                                              24.100   OCH.sub.2 COOH                                                        24.101   OSO.sub.2 CH.sub.3                                                    24.102   OSO.sub.2 CF.sub.3                                                    24.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       24.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               24.105   CH.sub.2 CHClCONHOH                                                   24.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              24.107   CH.sub.2 CH(CH.sub.3)COOH                                             24.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               24.109                                                                                   ##STR193##                                                           24.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            24.111                                                                                   ##STR194##                                                           24.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            24.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     24.114                                                                                   ##STR195##                                                           ______________________________________                                    

                  TABLE 25                                                         ______________________________________                                         Compounds of formula Iz                                                         ##STR196##                   (Iz)                                             Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         25.1     H                                                                     25.2     CN                                                                    25.3     OCH.sub.3                                                             25.4     NHSO.sub.2 CH.sub.3                                                   25.5     OC.sub.3 H.sub.7 (iso)                                                25.6     O-propargyl                                                           25.7     OCH(CH.sub.3)C.tbd.CH                                                 25.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        25.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          25.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 25.11    OCH.sub.2 COOCH.sub.3                                                 25.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     25.13    OCH.sub.2 COO-benzyl                                                  25.14    OCH(CH.sub.3)COObenzyl                                                25.15    SC.sub.3 H.sub.7 (iso)                                                25.16    SCH.sub.2 COOCH.sub.3                                                 25.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          25.18    SCH(CH.sub.3)COObenzyl                                                25.19    SCH.sub.2 COObenzyl                                                   25.20    COOCH.sub.3                                                           25.21    COOC.sub.3 H.sub.7 (iso)                                              25.22    COOC(CH.sub.3).sub.2 COOH                                             25.23    COOC(CH.sub.3).sub.2 COO-allyl                                        25.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      25.25    COOC(CH.sub.3).sub.2 COOethyl                                         25.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       25.27    CH.sub.2 CHClCOOethyl                                                 25.28    CH.sub.2 CH═CH.sub.2                                              25.29    CH.sub.2 CH.sub.2 CH.sub.3                                            25.30    CH.sub.2 CH.sub.2 CF.sub.3                                            25.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   25.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   25.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 25.34    CH.sub.2 CHClCOOH                                                     25.35    CH.sub.2 CHClCOOCH.sub.3                                              25.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 25.37    CH.sub.2 CHClCONHallyl                                                25.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            25.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     25.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           25.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          25.42    CH.sub.2 CH.sub.2 COOH                                                25.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         25.44    CH.sub.2 CH.sub.2 COOEt                                               25.45    CHClCHClCOOH                                                          25.46    CHClCHClCOOCH.sub.3                                                   25.47    CHClCHClCOOEt                                                         25.48    CH.sub.2 CH(OCH.sub.3)COOH                                            25.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     25.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           25.51    CH.sub.2 CH(SCH.sub.3)COOH                                            25.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     25.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           25.54    CH═CHCOOH                                                         25.55    CH═CHCOOCH.sub.3                                                  25.56    CH═CHCOOEt                                                        25.57    CH═CClCOOH                                                        25.58    CH═CClCOOCH.sub.3                                                 25.59    COOEt                                                                 25.60    CONH.sub.2                                                            25.61                                                                                    ##STR197##                                                           25.62    CONHSO.sub.2 CH.sub.3                                                 25.63    COOCH.sub.2 COOH                                                      25.64    COOCH.sub.2 COOCH.sub.3                                               25.65    COOCH(CH.sub.3)COOH                                                   25.66    COOCH(CH.sub.3)COOCH.sub.3                                            25.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          25.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   25.69    COOC(CH.sub.3).sub.2 CN                                               25.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        25.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   25.72                                                                                    ##STR198##                                                           25.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               25.74    COOCH.sub.2 C.tbd.CH                                                  25.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             25.76    COOCH(CH.sub.3)C.tbd.CH                                               25.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       25.78    NHallyl                                                               25.79    N(COCH.sub.3)allyl                                                    25.80    N(Et)SO.sub.2 CH.sub.3                                                25.81    N(allyl)SO.sub.2 CH.sub.3                                             25.82    N(allyl)SO.sub.2 Et                                                   25.83    SO.sub.2 N(CH.sub.3).sub.2                                            25.84    SO.sub.2 NH.sub.2                                                     25.85    SO.sub.2 NHCOCH.sub.3                                                 25.86    OH                                                                    25.87    OEt                                                                   25.88    Oallyl                                                                25.89    OCH.sub.2 C.tbd.CCH.sub.3                                             25.90    OCH(CH.sub.3)CH═CH.sub.2                                          25.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 25.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       25.93                                                                                    ##STR199##                                                           25.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         25.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              25.96    OCH.sub.2 CH.sub.2 COOH                                               25.97    OC(CH.sub.3).sub.2 COOH                                               25.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        25.99    OC(CH.sub.3).sub.2 COOEt                                              25.100   OCH.sub.2 COOH                                                        25.101   OSO.sub.2 CH.sub.3                                                    25.102   OSO.sub.2 CF.sub.3                                                    25.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       25.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               25.105   CH.sub.2 CHClCONHOH                                                   25.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              25.107   CH.sub.2 CH(CH.sub.3)COOH                                             25.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               25.109                                                                                   ##STR200##                                                           25.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            25.111                                                                                   ##STR201##                                                           25.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            25.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     25.114                                                                                   ##STR202##                                                           ______________________________________                                    

                  TABLE 26                                                         ______________________________________                                         Compounds of formula Izz                                                        ##STR203##                   (Izz)                                            Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         26.1     H                                                                     26.2     CN                                                                    26.3     OCH.sub.3                                                             26.4     NHSO.sub.2 CH.sub.3                                                   26.5     OC.sub.3 H.sub.7 (iso)                                                26.6     O-propargyl                                                           26.7     OCH(CH.sub.3)C.tbd.CH                                                 26.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        26.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          26.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 26.11    OCH.sub.2 COOCH.sub.3                                                 26.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     26.13    OCH.sub.2 COO-benzyl                                                  26.14    OCH(CH.sub.3)COObenzyl                                                26.15    SC.sub.3 H.sub.7 (iso)                                                26.16    SCH.sub.2 COOCH.sub.3                                                 26.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          26.18    SCH(CH.sub.3)COObenzyl                                                26.19    SCH.sub.2 COObenzyl                                                   26.20    COOCH.sub.3                                                           26.21    COOC.sub.3 H.sub.7 (iso)                                              26.22    COOC(CH.sub.3).sub.2 COOH                                             26.23    COOC(CH.sub.3).sub.2 COO-allyl                                        26.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      26.25    COOC(CH.sub.3).sub.2 COOethyl                                         26.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       26.27    CH.sub.2 CHClCOOethyl                                                 26.28    CH.sub.2 CH═CH.sub.2                                              26.29    CH.sub.2 CH.sub.2 CH.sub.3                                            26.30    CH.sub.2 CH.sub.2 CF.sub.3                                            26.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   26.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   26.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 26.34    CH.sub.2 CHClCOOH                                                     26.35    CH.sub.2 CHClCOOCH.sub.3                                              26.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 26.37    CH.sub.2 CHClCONHallyl                                                26.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            26.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     26.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           26.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          26.42    CH.sub.2 CH.sub.2 COOH                                                26.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         26.44    CH.sub.2 CH.sub.2 COOEt                                               26.45    CHClCHClCOOH                                                          26.46    CHClCHClCOOCH.sub.3                                                   26.47    CHClCHClCOOEt                                                         26.48    CH.sub.2 CH(OCH.sub.3)COOH                                            26.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     26.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           26.51    CH.sub.2 CH(SCH.sub.3)COOH                                            26.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     26.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           26.54    CH═CHCOOH                                                         26.55    CH═CHCOOCH.sub.3                                                  26.56    CH═CHCOOEt                                                        26.57    CH═CClCOOH                                                        26.58    CH═CClCOOCH.sub.3                                                 26.59    COOEt                                                                 26.60    CONH.sub.2                                                            26.61                                                                                    ##STR204##                                                           26.62    CONHSO.sub.2 CH.sub.3                                                 26.63    COOCH.sub.2 COOH                                                      26.64    COOCH.sub.2 COOCH.sub.3                                               26.65    COOCH(CH.sub.3)COOH                                                   26.66    COOCH(CH.sub.3)COOCH.sub.3                                            26.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          26.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   26.69    COOC(CH.sub.3).sub.2 CN                                               26.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        26.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   26.72                                                                                    ##STR205##                                                           26.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               26.74    COOCH.sub.2 C.tbd.CH                                                  26.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             26.76    COOCH(CH.sub.3)C.tbd.CH                                               26.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       26.78    NHallyl                                                               26.79    N(COCH.sub.3)allyl                                                    26.80    N(Et)SO.sub.2 CH.sub.3                                                26.81    N(allyl)SO.sub.2 CH.sub.3                                             26.82    N(allyl)SO.sub.2 Et                                                   26.83    SO.sub.2 N(CH.sub.3).sub.2                                            26.84    SO.sub.2 NH.sub.2                                                     26.85    SO.sub.2 NHCOCH.sub.3                                                 26.86    OH                                                                    26.87    OEt                                                                   26.88    Oallyl                                                                26.89    OCH.sub.2 C.tbd.CCH.sub.3                                             26.90    OCH(CH.sub.3)CH═CH.sub.2                                          26.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 26.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       26.93                                                                                    ##STR206##                                                           26.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         26.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              26.96    OCH.sub.2 CH.sub.2 COOH                                               26.97    OC(CH.sub.3).sub.2 COOH                                               26.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        26.99    OC(CH.sub.3).sub.2 COOEt                                              26.100   OCH.sub.2 COOH                                                        26.101   OSO.sub.2 CH.sub.3                                                    26.102   OSO.sub.2 CF.sub.3                                                    26.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       26.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               26.105   CH.sub.2 CHClCONHOH                                                   26.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              26.107   CH.sub.2 CH(CH.sub.3)COOH                                             26.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               26.109                                                                                   ##STR207##                                                           26.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            26.111                                                                                   ##STR208##                                                           26.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            26.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     26.114                                                                                   ##STR209##                                                           ______________________________________                                    

                  TABLE 27                                                         ______________________________________                                         Compounds of formula Iyy                                                        ##STR210##                   (Iyy)                                            Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         27.1     H                                                                     27.2     CN                                                                    27.3     OCH.sub.3                                                             27.4     NHSO.sub.2 CH.sub.3                                                   27.5     OC.sub.3 H.sub.7 (iso)                                                27.6     O-propargyl                                                           27.7     OCH(CH.sub.3)C.tbd.CH                                                 27.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        27.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          27.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 27.11    OCH.sub.2 COOCH.sub.3                                                 27.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     27.13    OCH.sub.2 COO-benzyl                                                  27.14    OCH(CH.sub.3)COObenzyl                                                27.15    SC.sub.3 H.sub.7 (iso)                                                27.16    SCH.sub.2 COOCH.sub.3                                                 27.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          27.18    SCH(CH.sub.3)COObenzyl                                                27.19    SCH.sub.2 COObenzyl                                                   27.20    COOCH.sub.3                                                           27.21    COOC.sub.3 H.sub.7 (iso)                                              27.22    COOC(CH.sub.3).sub.2 COOH                                             27.23    COOC(CH.sub.3).sub.2 COO-allyl                                        27.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      27.25    COOC(CH.sub.3).sub.2 COOethyl                                         27.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       27.27    CH.sub.2 CHClCOOethyl                                                 27.28    CH.sub.2 CH═CH.sub.2                                              27.29    CH.sub.2 CH.sub.2 CH.sub.3                                            27.30    CH.sub.2 CH.sub.2 CF.sub.3                                            27.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   27.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   27.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 27.34    CH.sub.2 CHClCOOH                                                     27.35    CH.sub.2 CHClCOOCH.sub.3                                              27.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 27.37    CH.sub.2 CHClCONHallyl                                                27.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            27.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     27.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           27.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          27.42    CH.sub.2 CH.sub.2 COOH                                                27.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         27.44    CH.sub.2 CH.sub.2 COOEt                                               27.45    CHClCHClCOOH                                                          27.46    CHClCHClCOOCH.sub.3                                                   27.47    CHClCHClCOOEt                                                         27.48    CH.sub.2 CH(OCH.sub.3)COOH                                            27.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     27.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           27.51    CH.sub.2 CH(SCH.sub.3)COOH                                            27.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     27.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           27.54    CH═CHCOOH                                                         27.55    CH═CHCOOCH.sub.3                                                  27.56    CH═CHCOOEt                                                        27.57    CH═CClCOOH                                                        27.58    CH═CClCOOCH.sub.3                                                 27.59    COOEt                                                                 27.60    CONH.sub.2                                                            27.61                                                                                    ##STR211##                                                           27.62    CONHSO.sub.2 CH.sub.3                                                 27.63    COOCH.sub.2 COOH                                                      27.64    COOCH.sub.2 COOCH.sub.3                                               27.65    COOCH(CH.sub.3)COOH                                                   27.66    COOCH(CH.sub.3)COOCH.sub.3                                            27.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          27.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   27.69    COOC(CH.sub.3).sub.2 CN                                               27.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        27.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   27.72                                                                                    ##STR212##                                                           27.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               27.74    COOCH.sub.2 C.tbd.CH                                                  27.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             27.76    COOCH(CH.sub.3)C.tbd.CH                                               27.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       27.78    NHallyl                                                               27.79    N(COCH.sub.3)allyl                                                    27.80    N(Et)SO.sub.2 CH.sub.3                                                27.81    N(allyl)SO.sub.2 CH.sub.3                                             27.82    N(allyl)SO.sub.2 Et                                                   27.83    SO.sub.2 N(CH.sub.3).sub.2                                            27.84    SO.sub.2 NH.sub.2                                                     27.85    SO.sub.2 NHCOCH.sub.3                                                 27.86    OH                                                                    27.87    OEt                                                                   27.88    Oallyl                                                                27.89    OCH.sub.2 C.tbd.CCH.sub.3                                             27.90    OCH(CH.sub.3)CH═CH.sub.2                                          27.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 27.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       27.93                                                                                    ##STR213##                                                           27.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         27.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              27.96    OCH.sub.2 CH.sub.2 COOH                                               27.97    OC(CH.sub.3).sub.2 COOH                                               27.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        27.99    OC(CH.sub.3).sub.2 COOEt                                              27.100   OCH.sub.2 COOH                                                        27.101   OSO.sub.2 CH.sub.3                                                    27.102   OSO.sub.2 CF.sub.3                                                    27.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       27.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               27.105   CH.sub.2 CHClCONHOH                                                   27.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              27.107   CH.sub.2 CH(CH.sub.3)COOH                                             27.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               27.109                                                                                   ##STR214##                                                           27.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            27.111                                                                                   ##STR215##                                                           27.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            27.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     27.114                                                                                   ##STR216##                                                           ______________________________________                                    

                  TABLE 28                                                         ______________________________________                                         Compounds of formula lww                                                                                     (lww)                                             ##STR217##                                                                    Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         28.1     H                                                                     28.2     CN                                                                    28.3     OCH.sub.3                                                             28.4     NHSO.sub.2 CH.sub.3                                                   28.5     OC.sub.3 H.sub.7 (iso)                                                28.6     O-propargyl                                                           28.7     OCH(CH.sub.3)C.tbd.CH                                                 28.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        28.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          28.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 28.11    OCH.sub.2 COOCH.sub.3                                                 28.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     28.13    OCH.sub.2 COO-benzyl                                                  28.14    OCH(CH.sub.3)COObenzyl                                                28.15    SC.sub.3 H.sub.7 (iso)                                                28.16    SCH.sub.2 COOCH.sub.3                                                 28.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          28.18    SCH(CH.sub.3)COObenzyl                                                28.19    SCH.sub.2 COObenzyl                                                   28.20    COOCH.sub.3                                                           28.21    COOC.sub.3 H.sub.7 (iso)                                              28.22    COOC(CH.sub.3).sub.2 COOH                                             28.23    COOC(CH.sub.3).sub.2 COO-allyl                                        28.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      28.25    COOC(CH.sub.3).sub.2 COOethyl                                         28.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       28.27    CH.sub.2 CHClCOOethyl                                                 28.28    CH.sub.2 CH═CH.sub.2                                              28.29    CH.sub.2 CH.sub.2 CH.sub.3                                            28.30    CH.sub.2 CH.sub.2 CF.sub.3                                            28.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   28.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   28.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 28.34    CH.sub.2 CHClCOOH                                                     28.35    CH.sub.2 CHClCOOCH.sub.3                                              28.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 28.37    CH.sub.2 CHClCONHallyl                                                28.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            28.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     28.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           28.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          28.42    CH.sub.2 CH.sub.2 COOH                                                28.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         28.44    CH.sub.2 CH.sub.2 COOEt                                               28.45    CHClCHClCOOH                                                          28.46    CHClCHClCOOCH.sub.3                                                   28.47    CHClCHClCOOEt                                                         28.48    CH.sub.2 CH(OCH.sub.3)COOH                                            28.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     28.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           28.51    CH.sub.2 CH(SCH.sub.3)COOH                                            28.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     28.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           28.54    CH═CHCOOH                                                         28.55    CH═CHCOOCH.sub.3                                                  28.56    CH═CHCOOEt                                                        28.57    CH═CClCOOH                                                        28.58    CH═CClCOOCH.sub.3                                                 28.59    COOEt                                                                 28.60    CONH.sub.2                                                            28.61                                                                                    ##STR218##                                                           28.62    CONHSO.sub.2 CH.sub.3                                                 28.63    COOCH.sub.2 COOH                                                      28.64    COOCH.sub.2 COOCH.sub.3                                               28.65    COOCH(CH.sub.3)COOH                                                   28.66    COOCH(CH.sub.3)COOCH.sub.3                                            28.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          28.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   28.69    COOC(CH.sub.3).sub.2 CN                                               28.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        28.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   28.72                                                                                    ##STR219##                                                           28.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               28.74    COOCH.sub.2 C.tbd.CH                                                  28.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             28.76    COOCH(CH.sub.3)C.tbd.CH                                               28.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       28.78    NHallyl                                                               28.79    N(COCH.sub.3)allyl                                                    28.80    N(Et)SO.sub.2 CH.sub.3                                                28.81    N(allyl)SO.sub.2 CH.sub.3                                             28.82    N(allyl)SO.sub.2 Et                                                   28.83    SO.sub.2 N(CH.sub.3).sub.2                                            28.84    SO.sub.2 NH.sub.2                                                     28.85    SO.sub.2 NHCOCH.sub.3                                                 28.86    OH                                                                    28.87    OEt                                                                   28.88    Oallyl                                                                28.89    OCH.sub.2 C.tbd.CCH.sub.3                                             28.90    OCH(CH.sub.3)CH═CH.sub.2                                          28.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 28.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       28.93                                                                                    ##STR220##                                                           28.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         28.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              28.96    OCH.sub.2 CH.sub.2 COOH                                               28.97    OC(CH.sub.3).sub.2 COOH                                               28.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        28.99    OC(CH.sub.3).sub.2 COOEt                                              28.100   OCH.sub.2 COOH                                                        28.101   OSO.sub.2 CH.sub.3                                                    28.102   OSO.sub.2 CF.sub.3                                                    28.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       28.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               28.105   CH.sub.2 CHClCONHOH                                                   28.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              28.107   CH.sub.2 CH(CH.sub.3)COOH                                             28.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               28.109                                                                                   ##STR221##                                                           28.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            28.111                                                                                   ##STR222##                                                           28.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            28.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     28.114                                                                                   ##STR223##                                                           ______________________________________                                    

                  TABLE 29                                                         ______________________________________                                         Compounds of formula lvv                                                                                     (lvv)                                             ##STR224##                                                                    Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         29.1     H                                                                     29.2     CN                                                                    29.3     OCH.sub.3                                                             29.4     NHSO.sub.2 CH.sub.3                                                   29.5     OC.sub.3 H.sub.7 (iso)                                                29.6     O-propargyl                                                           29.7     OCH(CH.sub.3)C.tbd.CH                                                 29.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        29.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          29.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 29.11    OCH.sub.2 COOCH.sub.3                                                 29.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     29.13    OCH.sub.2 COO-benzyl                                                  29.14    OCH(CH.sub.3)COObenzyl                                                29.15    SC.sub.3 H.sub.7 (iso)                                                29.16    SCH.sub.2 COOCH.sub.3                                                 29.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          29.18    SCH(CH.sub.3)COObenzyl                                                29.19    SCH.sub.2 COObenzyl                                                   29.20    COOCH.sub.3                                                           29.21    COOC.sub.3 H.sub.7 (iso)                                              29.22    COOC(CH.sub.3).sub.2 COOH                                             29.23    COOC(CH.sub.3).sub.2 COO-allyl                                        29.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      29.25    COOC(CH.sub.3).sub.2 COOethyl                                         29.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       29.27    CH.sub.2 CHClCOOethyl                                                 29.28    CH.sub.2 CH═CH.sub.2                                              29.29    CH.sub.2 CH.sub.2 CH.sub.3                                            29.30    CH.sub.2 CH.sub.2 CF.sub.3                                            29.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   29.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   29.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 29.34    CH.sub.2 CHClCOOH                                                     29.35    CH.sub.2 CHClCOOCH.sub.3                                              29.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 29.37    CH.sub.2 CHClCONHallyl                                                29.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            29.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     29.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           29.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          29.42    CH.sub.2 CH.sub.2 COOH                                                29.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         29.44    CH.sub.2 CH.sub.2 COOEt                                               29.45    CHClCHClCOOH                                                          29.46    CHClCHClCOOCH.sub.3                                                   29.47    CHClCHClCOOEt                                                         29.48    CH.sub.2 CH(OCH.sub.3)COOH                                            29.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     29.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           29.51    CH.sub.2 CH(SCH.sub.3)COOH                                            29.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     29.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           29.54    CH═CHCOOH                                                         29.55    CH═CHCOOCH.sub.3                                                  29.56    CH═CHCOOEt                                                        29.57    CH═CClCOOH                                                        29.58    CH═CClCOOCH.sub.3                                                 29.59    COOEt                                                                 29.60    CONH.sub.2                                                            29.61                                                                                    ##STR225##                                                           29.62    CONHSO.sub.2 CH.sub.3                                                 29.63    COOCH.sub.2 COOH                                                      29.64    COOCH.sub.2 COOCH.sub.3                                               29.65    COOCH(CH.sub.3)COOH                                                   29.66    COOCH(CH.sub.3)COOCH.sub.3                                            29.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          29.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   29.69    COOC(CH.sub.3).sub.2 CN                                               29.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        29.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   29.72                                                                                    ##STR226##                                                           29.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               29.74    COOCH.sub.2 C.tbd.CH                                                  29.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             29.76    COOCH(CH.sub.3)C.tbd.CH                                               29.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       29.78    NHallyl                                                               29.79    N(COCH.sub.3)allyl                                                    29.80    N(Et)SO.sub.2 CH.sub.3                                                29.81    N(allyl)SO.sub.2 CH.sub.3                                             29.82    N(allyl)SO.sub.2 Et                                                   29.83    SO.sub.2 N(CH.sub.3).sub.2                                            29.84    SO.sub.2 NH.sub.2                                                     29.85    SO.sub.2 NHCOCH.sub.3                                                 29.86    OH                                                                    29.87    OEt                                                                   29.88    Oallyl                                                                29.89    OCH.sub.2 C.tbd.CCH.sub.3                                             29.90    OCH(CH.sub.3)CH═CH.sub.2                                          29.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 29.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       29.93                                                                                    ##STR227##                                                           29.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         29.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              29.96    OCH.sub.2 CH.sub.2 COOH                                               29.97    OC(CH.sub.3).sub.2 COOH                                               29.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        29.99    OC(CH.sub.3).sub.2 COOEt                                              29.100   OCH.sub.2 COOH                                                        29.101   OSO.sub.2 CH.sub.3                                                    29.102   OSO.sub.2 CF.sub.3                                                    29.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       29.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               29.105   CH.sub.2 CHClCONHOH                                                   29.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              29.107   CH.sub.2 CH(CH.sub.3)COOH                                             29.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               29.109                                                                                   ##STR228##                                                           29.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            29.111                                                                                   ##STR229##                                                           29.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            29.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     29.114                                                                                   ##STR230##                                                           ______________________________________                                    

                  TABLE 30                                                         ______________________________________                                         Compounds of formula luu                                                                                     (luu)                                             ##STR231##                                                                    Comp. No.                                                                               R.sub.6                 M.p.                                          ______________________________________                                         30.1     H                                                                     30.2     CN                                                                    30.3     OCH.sub.3                                                             30.4     NHSO.sub.2 CH.sub.3                                                   30.5     OC.sub.3 H.sub.7 (iso)                                                30.6     O-propargyl                                                           30.7     OCH(CH.sub.3)C.tbd.CH                                                 30.8     OCH.sub.2 COOCH.sub.2 CH.sub.3                                        30.9     OCH.sub.2 CH.sub.2 OCH.sub.3                                          30.10    OCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3                                 30.11    OCH.sub.2 COOCH.sub.3                                                 30.12    OCH.sub.2 COOC.sub.5 H.sub.11 (n)                                     30.13    OCH.sub.2 COO-benzyl                                                  30.14    OCH(CH.sub.3)COObenzyl                                                30.15    SC.sub.3 H.sub.7 (iso)                                                30.16    SCH.sub.2 COOCH.sub.3                                                 30.17    SCH.sub.2 COOC.sub.2 H.sub.5                                          30.18    SCH(CH.sub.3)COObenzyl                                                30.19    SCH.sub.2 COObenzyl                                                   30.20    COOCH.sub.3                                                           30.21    COOC.sub.3 H.sub.7 (iso)                                              30.22    COOC(CH.sub.3).sub.2 COOH                                             30.23    COOC(CH.sub.3).sub.2 COO-allyl                                        30.24    COOC(CH.sub.3).sub.2 COOCH.sub.3                                      30.25    COOC(CH.sub.3).sub.2 COOethyl                                         30.26    COOC(CH.sub.3).sub.2 CONH-allyl                                       30.27    CH.sub.2 CHClCOOethyl                                                 30.28    CH.sub.2 CH═CH.sub.2                                              30.29    CH.sub.2 CH.sub.2 CH.sub.3                                            30.30    CH.sub.2 CH.sub.2 CF.sub.3                                            30.31    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R)                                   30.32    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (S)                                   30.33    OCH(CH.sub.3)COOC.sub.2 H.sub.5 (R,S)                                 30.34    CH.sub.2 CHClCOOH                                                     30.35    CH.sub.2 CHClCOOCH.sub.3                                              30.36    CH.sub.2 CHClCOOC.sub.3 H.sub.7 (iso)                                 30.37    CH.sub.2 CHClCONHallyl                                                30.38    CH.sub.2 C(CH.sub.3)ClCOOH                                            30.39    CH.sub.2 C(CH.sub.3)ClCOOCH.sub.3                                     30.40    CH.sub.2 C(CH.sub.3)ClCOOEt                                           30.41    CH.sub.2 C(CH.sub.3)ClCONHEt                                          30.42    CH.sub.2 CH.sub.2 COOH                                                30.43    CH.sub.2 CH.sub.2 COOCH.sub.3                                         30.44    CH.sub.2 CH.sub.2 COOEt                                               30.45    CHClCHClCOOH                                                          30.46    CHClCHClCOOCH.sub.3                                                   30.47    CHClCHClCOOEt                                                         30.48    CH.sub.2 CH(OCH.sub.3)COOH                                            30.49    CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                     30.50    CH.sub.2 CH(OCH.sub.3)COOEt                                           30.51    CH.sub.2 CH(SCH.sub.3)COOH                                            30.52    CH.sub.2 CH(SCH.sub.3)COOCH.sub.3                                     30.53    CH.sub.2 CH(SCH.sub.3)COOEt                                           30.54    CH═CHCOOH                                                         30.55    CH═CHCOOCH.sub.3                                                  30.56    CH═CHCOOEt                                                        30.57    CH═CClCOOH                                                        30.58    CH═CClCOOCH.sub.3                                                 30.59    COOEt                                                                 30.60    CONH.sub.2                                                            30.61                                                                                    ##STR232##                                                           30.62    CONHSO.sub.2 CH.sub.3                                                 30.63    COOCH.sub.2 COOH                                                      30.64    COOCH.sub.2 COOCH.sub.3                                               30.65    COOCH(CH.sub.3)COOH                                                   30.66    COOCH(CH.sub.3)COOCH.sub.3                                            30.67    COOCH(CH.sub.3)CH.sub.2 COOH                                          30.68    COOCH(CH.sub.3)CH.sub.2 COOCH.sub.3                                   30.69    COOC(CH.sub.3).sub.2 CN                                               30.70    COOCH.sub.2 CH.sub.2 OCH.sub.3                                        30.71    COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OCH.sub.3                   30.72                                                                                    ##STR233##                                                           30.73    COOC(CH.sub.3).sub.2 COOCH.sub.2 PHENYL                               30.74    COOCH.sub.2 C.tbd.CH                                                  30.75    COOC(CH.sub.3).sub.2 COOCH.sub.2 C.tbd.CH                             30.76    COOCH(CH.sub.3)C.tbd.CH                                               30.77    COOC(CH.sub.3).sub.2 COCH.sub.3                                       30.78    NHallyl                                                               30.79    N(COCH.sub.3)allyl                                                    30.80    N(Et)SO.sub.2 CH.sub.3                                                30.81    N(allyl)SO.sub.2 CH.sub.3                                             30.82    N(allyl)SO.sub.2 Et                                                   30.83    SO.sub.2 N(CH.sub.3).sub.2                                            30.84    SO.sub.2 NH.sub.2                                                     30.85    SO.sub.2 NHCOCH.sub.3                                                 30.86    OH                                                                    30.87    OEt                                                                   30.88    Oallyl                                                                30.89    OCH.sub.2 C.tbd.CCH.sub.3                                             30.90    OCH(CH.sub.3)CH═CH.sub.2                                          30.91    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                 30.92    OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                       30.93                                                                                    ##STR234##                                                           30.94    OCH.sub.2 CH.sub.2 NHCH.sub.3                                         30.95    OCH.sub.2 CH.sub.2 N(CH.sub.3)COCH.sub.3                              30.96    OCH.sub.2 CH.sub.2 COOH                                               30.97    OC(CH.sub.3).sub.2 COOH                                               30.98    OC(CH.sub.3).sub.2 COOCH.sub.3                                        30.99    OC(CH.sub.3).sub.2 COOEt                                              30.100   OCH.sub.2 COOH                                                        30.101   OSO.sub.2 CH.sub.3                                                    30.102   OSO.sub.2 CF.sub.3                                                    30.103   CH.sub.2 CHClCOOC.sub.2 H.sub.5                                       30.104   CH.sub.2 CHClCON(C.sub.2 H.sub.5).sub.2                               30.105   CH.sub.2 CHClCONHOH                                                   30.106   CH.sub.2 CHClCOOCH.sub.2 C.sub.6 H.sub.5                              30.107   CH.sub.2 CH(CH.sub.3)COOH                                             30.108   CH.sub.2 CH(CH.sub.3)COOC.sub.2 H.sub.5                               30.109                                                                                   ##STR235##                                                           30.110   COOC(CH.sub.3).sub.2 COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            30.111                                                                                   ##STR236##                                                           30.112   COOC(CH.sub.3).sub.2 CONHCH.sub.2 C.tbd.CH                            30.113   COOC(CH.sub.3).sub.2 CON(CH.sub.2 CH.sub.3).sub.2                     30.114                                                                                   ##STR237##                                                           ______________________________________                                    

Formulation Examples for active ingredients of formula I (throughout, percentages are by weight)

    ______________________________________                                         F1. Emulsifiable concentrates                                                                       a)     b)     c)   d)                                     ______________________________________                                         a compound of Tables 1-30                                                                           5%     10%    25%  50%                                    calcium dodecylbenzenesulfonate                                                                     6%      8%     6%   8%                                    castor oil polyglycol ether (36 mol of                                                              4%     --      4%   4%                                    ethylene oxide)                                                                octylphenol polyglycol ether (7-8 mol of                                                            --      4%    --    2%                                    ethylene oxide)                                                                cylohexanone         --     --     10%  20%                                    aromatic hydrocarbon mixture C.sub.9 -C.sub.12                                                      85%    78%    55%  16%                                    ______________________________________                                    

Emulsions of any desired concentration can be obtained from such concentrates by dilution with water.

    ______________________________________                                         F2. Solutions        a)     b)     c)   d)                                     ______________________________________                                         a compound of Tables 1-30                                                                            5%    10%    50%  90%                                    1-methoxy-3-(3-methoxy-propoxy)-propane                                                             --     20%    20%  --                                     polyethylene glycol (mol. wt. 400)                                                                  20%    10%    --   --                                     N-methyl-2-pyrrolidone                                                                              --     --     30%  10%                                    aromatic hydrocarbon mixture C.sub.9 -C.sub.12                                                      75%    60%    --   --                                     ______________________________________                                    

The solutions are suitable for application in the form of micro-drops.

    ______________________________________                                         F3. Wettable powders a)     b)     c)   d)                                     ______________________________________                                         a compound of Tables 1-30                                                                           5%     25%    50%  80%                                    sodium lignosulfonate                                                                               4%     --     3%   --                                     sodium laurylsulfate 2%     3%     --    4%                                    sodium diisobutylnaphthalenesulfonate                                                               --     6%     5%    6%                                    octylphenol polyglycol ether (7-8 mol of                                                            --     1%     2%   --                                     ethylene oxide)                                                                highly dispersed silicic acid                                                                       1%     3%     5%   10%                                    kaolin               88%    62%    35%  --                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.

    ______________________________________                                         F4. Coated granules a)       b)      c)                                        ______________________________________                                         a compound of Tables 1-30                                                                          0.1%     5%      15%                                       highly dispersed silicic acid                                                                      0.9%     2%       2%                                       inorganic carrier (diameter 0.1-1 mm) e.g.                                                         99.0%    93%     83%                                       CaCO.sub.3 or SiO.sub.2                                                        ______________________________________                                    

The active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.

    ______________________________________                                         F5. Coated granules a)       b)      c)                                        ______________________________________                                         a compound of Tables 1-30                                                                          0.1%     5%      15%                                       polyethylene glycol (mol. wt. 200)                                                                 1.0%     2%       3%                                       highly dispersed silicic acid                                                                      0.9%     1%       2%                                       inorganic carrier (diameter 0.1-1 mm) e.g.                                                         98.0%    92%     80%                                       CaCO.sub.3 or SiO.sub.2                                                        ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

    ______________________________________                                         F6. Extruder granules                                                                          a)      b)       c)   d)                                       ______________________________________                                         a compound of Tables 1-30                                                                      0.1%    3%       5%   15%                                      sodium lignosulfonate                                                                          1.5%    2%       3%    4%                                      carboxymethylcellulose                                                                         1.4%    2%       2%    2%                                      kaolin          97.0%   93%      90%  79%                                      ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

    ______________________________________                                         F7. Dusts       a)         b)     c)                                           ______________________________________                                         a compound of Tables 1-30                                                                       0.1%       1%     5%                                          talcum          39.9%      49%    35%                                          kaolin          60.0%      50%    60%                                          ______________________________________                                    

Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.

    ______________________________________                                         F8. Suspension concentrates                                                                     a)      b)      c)    d)                                      ______________________________________                                         a compound of Tables 1-30                                                                       3%      10%     25%   50%                                     ethylene glycol  5%      5%      5%    5%                                      nonylphenol polyglycol ether (15                                                                --      1%      2%    --                                      mol of ethylene oxide)                                                         sodium lignosulfonate                                                                           3%      3%      4%    5%                                      carboxymethylcellulose                                                                          1%      1%      1%    1%                                      37% aqueous formaldehyde                                                                        0.2%    0.2%    0.2%  0.2%                                    solution                                                                       silicone oil emulsion                                                                           0.8%    0.8%    0.8%  0.8%                                    water            87%     79%     62%   38%                                     ______________________________________                                    

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension cencentrate from which suspensions of any desired concentration can be obtained by dilution with water.

BIOLOGICAL EXAMPLES Example B1: Pre-emergence herbicidal action

Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic pots. Immediately after sowing, an aqueous suspension or emulsion of the test compounds prepared from a 25% wettable powder or emulsifiable concentrate (Example F3, b) or F1, c) is applied by spraying at a rate of application corresponding to 2000 g of active ingredient/hectare (500 l water/ha). The test plants are then cultivated in a greenhouse under optimum conditions. After 3 weeks the test is evaluated in accordance with a scale of nine ratings (1=total damage, 9=no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.

Test plants: Avena, Setaria, Sinapis, Stellaria

The compounds according to the invention exhibit good herbicidal action.

Examples of the good herbicidal action are given in Table B1.

                  TABLE B1                                                         ______________________________________                                         Pre-emergence action:                                                                    Test plant:                                                          Compound No.                                                                               Avena   Setaria   Sinapis                                                                              Stellaria                                  ______________________________________                                         1.001       1       1         1     1                                          1.007       1       1         2     1                                          1.010       2       1         2     1                                          2.007       2       1         2     1                                          2.035       2       1         2     1                                          2.037       2       1         1     1                                          3.001       1       1         1     1                                          3.010       3       1         1     1                                          3.011       2       1         1     1                                          3.035       2       2         1     1                                          7.001       5       1         1     3                                          8.001       5       1         4     3                                          8.009       3       1         2     2                                          9.007       3       1         2     1                                          ______________________________________                                    

The same results are obtained when compounds of formula I are formulated in accordance with Examples F2 and F4 to F8.

Example B2: Post-emergence herbicidal action (contact herbicide)

In a greenhouse, monocotyledonous and dicotyledonous test plants are raised in plastic pots, containing standard soil and at the 4- to 6-leaf stage are sprayed with an aqueous suspension or emulsion of the test compounds of formula I prepared from a 25% wettable powder or emulsifiable concentrate (Example F3, b) or F1, c)) at a rate of application corresponding to 2000 g of active ingredient/ha (500 l water/ha). The test plants are then grown on in the greenhouse under optimum conditions. After about 18 days the test is evaluated in accordance with a scale of nine ratings (1=total damage, 9=no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.

In this test too, the compounds of formula I according to the invention exhibit good herbicidal action.

Examples of the good herbicidal activity of the compounds of formula I are given in Table B2.

                  TABLE B2                                                         ______________________________________                                         Post-emergence action:                                                                   Test plant:                                                          Compound No.                                                                               Avena   Setaria   Sinapis                                                                              Stellaria                                  ______________________________________                                         1.001       1       1         1     1                                          1.007       1       1         1     1                                          1.010       2       1         1     1                                          1.042       1       1         1     1                                          1.044       5       2         1     1                                          2.001       1       1         1     1                                          2.007       2       1         1     1                                          2.037       1       1         1     1                                          2.038       1       1         1     1                                          2.039       1       1         1     1                                          2.041       5       2         1     1                                          3.001       1       1         1     1                                          3.010       2       1         1     1                                          3.011       1       1         1     1                                          3.035       1       1         1     1                                          3.037       1       1         1     1                                          3.039       1       1         1     1                                          3.041       6       2         1     1                                          7.001       6       2         2     2                                          7.034       2       1         1     1                                          7.040       6       2         1     1                                          8.001       5       1         1     1                                          8.009       2       1         1     1                                          8.035       1       1         1     1                                          8.073       1       1         1     1                                          9.007       2       1         1     3                                          9.041       6       3         1     1                                          9.073       2       2         1     1                                          ______________________________________                                    

The same results are obtained when compounds of formula I are formulated in accordance with Examples F2 and F4 to F8. 

What is claimed is:
 1. A compound of formula I ##STR238## wherein R₂ is C₁ -C₂ alkyl;n is 0, 1 or 2; R₃ is C₁ -C₄ alkyl; R₄ is hydrogen, fluorine, or chlorine; R₅ is halogen, methyl or cyano; R₆ is(i) hydrogen, (ii) OR₂₀ in whichR₂₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynly, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, C₁ -C₈ alkyl-COXR₂₁, phenyl, benzyl, those aromatic rings being unsubstituted or mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, in which;X is oxygen, sulfur or NR₂₂ ; R₂₁ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl or by halogen; and R₂₂ is hydrogen, C₁ -C₈ alkyl or C₃ -C₈ alkenyl; (iii) COYR₅₀ in whichY is oxygen, sulfur, NR₅₁ or NOR₅₄, and R₅₀ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, benzyl mono-to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, C₁ -C₄ alkyl-COZR₅₂, in whichZ is oxygen, sulfur, NR₅₃ or NOR₅₆ ; R₅₂ is hydrogen, C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ alkoxy-C₁ -C₄ alkyl, C₁ -C₄ alkylthio-C₁ -C₄ alkyl, phenyl, phenyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; R₅₁ and R₅₃ are each independently of the other C₁ -C₈ alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₈ haloalkyl, C₁ -C₄ alkylcarbonyl, C₁ -C₄ haloalkylcarbonyl, C₁ -C₄ alkylsulfonyl, C₁ -C₄ haloalkylsulfonyl, benzoyl, benzoyl mono-to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen, benzyl, or benzyl mono- to tri-substituted by C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or by halogen; and R₅₄ and R₅₅ are each independently of the other C₁ -C₄ alkyl; or (iv) C₁ -C₄ alkyl-COZR₅₂, C₁ -C₄ haloalkyl-COZR₅₂, C₂ -C₄ alkenyl-COZR₅₂, C₃ -C₈ alkynyl-COZR₅₂, or the salts or stereoisomers thereof.
 2. A compound according to claim 1, wherein R₅ is chlorine, bromine, methyl or cyano.
 3. A compound according to claim 1, wherein n is 0 or
 2. 4. A compound according to claim 1, wherein R₂ is methyl.
 5. A compound according to claim 1, wherein R₃ is methyl or ethyl.
 6. A compound according to claim 1, wherein R₃ is methyl.
 7. A compound according to claim 1, wherein R₄ is fluorine.
 8. A compound according to claim 1, wherein R₄ is hydrogen.
 9. A compound according to claim 1, wherein R₄ is chlorine.
 10. A compound according to claim 1, wherein R₄ is chlorine; and R₆ is OR₂₀.
 11. A compound according to claim 1, wherein R₄ is fluorine; and R₆ is OR₂₀.
 12. A compound according to claim 1, wherein R₄ is chlorine; and R₆ is COYR₅₀, C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₃ -C₈ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂.
 13. A compound according to claim 1, wherein R₄ is fluorine; and R₆ is COYR₅₋, C₁ -C₄ alkylCOZR₅₂, C₁ -C₄ haloalkylCOZR₅₂, C₂ -C₄ alkenylCOZR₅₂, C₃ -C₈ alkynylCOZR₅₂ or C₂ -C₄ haloalkenylCOZR₅₂.
 14. A compound according to claim 1, wherein R₅ is chlorine; and R₆ is --COYR₅₀.
 15. A herbicidal and plant growth-inhibiting composition comprising one or more compounds of formula I according to claim
 1. 16. A composition according to claim 15, comprising from 0.1 to 95% of a compound of formula I.
 17. A method of controlling undesired plant growth, which comprises applying an effective amount of a compound of formula I, according to claim 1, or of a composition comprising such a compound, to the plants or to the locus thereof.
 18. A method according to claim 17, which comprises the application of a compound of formula I in an amount of from 0.001 to 2 kg per hectare.
 19. A method of inhibiting plant growth, which comprises applying an effective amount of a compound of formula I, according to claim 1, or of a composition comprising such a compound, to the plants or to the locus thereof. 